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DOI: 10.1055/s-0040-1720121
Recyclable Palladium-Catalyzed Carbonylative Coupling of Aryl Halides and Organoaluminum Compounds with tert-Butyl Isocyanide as CO Equivalent Leading to 1,2-Diketones
We thank the National Natural Science Foundation of China (No. 21664008) and Key Lab of Fluorine and Silicon for Energy Materials and Chemistry of Ministry of Education (No. KFSEMC-202206) and Key Project of Basic Research of Jiangxi Academy of Sciences for financial support.
Abstract
An efficient heterogeneous palladium-catalyzed carbonylative coupling of aryl halides and organoaluminum compounds has been developed using tert-butyl isocyanide as CO equivalent. The carbonylation reaction proceeds smoothly in toluene with KOtBu as a base at 100 °C by using 10 mol% of an SBA-15-anchored bidentate phosphine palladium(0) complex [2P-SBA-15-Pd(0)] as the catalyst and provides a general and practical approach for the assembly of 1,2-diketones in good to excellent yields. This heterogenized palladium catalyst can be readily separated and recovered via a simple centrifugation process and reused for more than seven cycles with almost consistent catalytic efficiency.
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Key words
palladium - carbonylative coupling - organoaluminum reagents - 1,2-diketones - heterogeneous catalysis1,2-Diketones constitute an important class of structural motifs with key applications in the construction of biologically active molecules and natural products.[1] [2] Furthermore, 1,2-diketone skeletons have been found to be present in some vital molecules with antitumor activities[3] and photochemical properties.[4] They have also been utilized as ligands for diverse metal complexes[5] and as versatile building blocks for the assembly of medicinal molecules[6] and heterocyclic compounds.[7] As a result, the synthesis of 1,2-diketones has attracted a great deal of interest, and many strategies for their preparation have been developed in recent years. Traditional routes to 1,2-diketones mainly involve the oxidation of different substrates such as ketone derivatives,[8] olefins,[9] and internal alkynes.[10] Additionally, Mn-mediated oxidative decarboxylative coupling of arylpropiolic acids with arylboronic acids[11] and Cu-catalyzed oxidative decarboxylative coupling of aryl iodides with arylpropiolic acids or cinnamic acids[12] also proved to be efficient approaches for the synthesis of 1,2-diketones. The reaction proceeds through a decarboxylative coupling and subsequent oxidation sequence. In spite of significant progress made in this field, the availability and prior preparation of the substrates in the aforementioned methods are incommodious. Thus, the development of a novel and more efficient synthetic strategy for 1,2-diketones from readily available starting materials under mild conditions is still highly desirable.
Palladium-catalyzed carbonylation of aryl halides has provided a powerful tool for the assembly of carbonyl-containing compounds.[13] Carbonylation of aryl halides in the synthesis of ketones is well established, but the reactions usually require the use of high-pressure CO, which can pose a safety risk in industry. Although the development of stable CO-releasing molecules has overcome safety challenges and attracted increasing interest in recent years, their application in large-scale syntheses or industry would be problematic in terms of both cost and environmental perspectives. The employment of isocyanide as a stoichiometric CO surrogate has emerged as an attractive alternative to other CO sources[14] and has been successfully applied in various carbonylation reactions such as carbonylative Sonogashira coupling and formylation of aryl halides.[15] Furthermore, transition-metal-catalyzed double isocyanide insertion reactions have been applied for the construction of heterocyclic compounds.[16] Recently, Dechert-Schmitt et al. reported an efficient approach for the assembly of unsymmetical 1,2-diketones via palladium-catalyzed carbonylative coupling of aryl(heteroaryl) halides and organozinc reagents with tert-butyl isocyanide as a CO equivalent.[17] Chen and Wu developed a palladium-catalyzed carbonylative coupling of aryl halides and organoaluminum reagents towards 1,2-diketones using tert-butyl isocyanide as the CO source.[18] Although the palladium-catalyzed carbonylative coupling of aryl halides with organometal reagents was highly efficient for the synthesis of 1,2-diketone derivatives, higher loadings (10 mol%) of palladium catalysts were used to achieve high yields.[17] [18] Moreover, industrial applications of homogeneous palladium complexes remain an important challenge as they are quite expensive, unrecyclable, and difficult to be completely removed from the final product, which is a particularly serious drawback for their application in the construction of pharmaceutical molecules. Covalently anchoring the existing palladium complexes onto an insoluble support is one of the most effective strategies to address these problems.[19] Despite much efforts devoted to the immobilization of homogeneous palladium complexes during the past few decades,[20] no example of carbonylative synthesis of 1,2-diketones catalyzed by the heterogenized palladium complexes has been reported to date. Therefore, the development of a recyclable heterogeneous palladium catalyst that allows for highly efficient assembly of 1,2-diketone derivatives via carbonylative coupling is worthwhile.
Mesoporous silica SBA-15 has been widely utilized as an ideal support for immobilizing homogeneous catalysts owing to its high surface area (600–900 m2/g), thicker pore walls, and greater stability in aqueous solutions compared to MCM-41.[21] SBA-15 has a hexagonal array of uniform channels with pore diameters between 5 and 30 nm, which are much larger than those of MCM-41 or MCM-48, thereby showing a much lower diffusion resistance.[22] Various transition-metal complexes such as iridium, platinum, gold, rhodium, palladium, and copper anchored onto SBA-15 have been successfully applied in diverse organic reactions.[23] In a continuation of our research interest in the development of recyclable catalytic systems for palladium-catalyzed carbonylative transformations,[24] herein we report a heterogeneous palladium-catalyzed carbonylative coupling of aryl halides and organoaluminum reagents using tert-butyl isocyanide as CO equivalent and an SBA-15-immobilized bidentate phosphine palladium(0) complex [2P-SBA-15-Pd(0)] as catalyst towards 1,2-diketone derivatives (Scheme [1]). This heterogenized palladium complex exhibits a comparable catalytic activity to the homogeneous PdCl2/ DPPP system and can be reused more than seven cycles without any significant loss of catalytic activity.
The mesoporous SBA-15-immobilized bidentate phosphine palladium(0) complex [2P-SBA-15-Pd(0)] was prepared according to the preparative route as shown in Scheme [2]. Firstly, the condensation reaction of (EtO)3Si(CH2)3NH2 with mesoporous silica SBA-15 in anhydrous toluene at reflux, followed by silylation with (Me3Si)2NH in anhydrous toluene at room temperature provided the aminopropyl-modified SBA-15 material (H2N-SBA-15). The latter was then reacted with HOCH2PPh2, generated in situ from paraformaldehyde and HPPh2 in toluene at reflux, to provide the bidentate phosphine ligand-functionalized SBA-15 material [2P-SBA-15]. Finally, the modified 2P-SBA-15 material was complexed with palladium chloride in acetone at reflux, followed by reduction with hydrazine hydrate in ethanol at room temperature to afford the SBA-15-immobilized bidentate phosphine palladium(0) complex [2P-SBA-15-Pd(0)] as a gray powder with Pd content of 0.49 mmol/g based on ICP-AES analysis. This new heterogenized bidentate phosphine palladium(0) complex was characterized by a range of physicochemical techniques (see the Supporting Information).
The 2P-SBA-15-Pd(0) complex was then utilized as a catalyst for carbonylative coupling of aryl halides and organoaluminum reagents with tert-butyl isocyanide as the CO source. Initial experiments with iodobenzene (1a) and trimethylaluminum (2a) as substrates were conducted to optimize reaction conditions with respect to solvents, bases, reaction temperatures, and palladium loadings; the results are summarized in Table [1]. First, the influence of different bases on the model reaction was tested by using 10 mol% of the 2P-SBA-15-Pd(0) complex as the catalyst in toluene at 100 °C (entries 1–7). It was found that KOtBu was the most efficient base and gave 1-phenylproane-1,2-dione (3a) in 79% yield (entry 3), while NaOtBu was less effective and other bases such as LiOtBu, Et3N, DBU, Cs2CO3, and K2CO3 proved to be ineffective (entries 1, 2, and 4–7). Replacement of toluene with THF, 1,4-dioxane, or MeCN resulted in a decreased yield of 3a, while DMF was found to be a poor solvent for the reaction (entries 8–11). Reducing the reaction temperature to 90 °C led to a remarkable drop in the yield of 3a (entry 12), whilst the reaction run at 110 °C did not give a better yield (entry 13). When the amount of tert-butyl isocyanide was decreased to 2.0 equiv (entry 14), the desired 3a was obtained in a lower yield of 71%. To demonstrate the advantage of SBA-15 over other solid supports, we also prepared a commercially available SiO2-immobilized bidentate phosphine palladium(0) complex [2P-SiO2-Pd(0)] by replacement of SBA-15 with fumed silica as the support in a similar procedure to that shown in Scheme [2]. When 10 mol% of 2P-SiO2-Pd(0) was used as the catalyst, the desired 3a was isolated in a lower yield of 68% (entry 15). Notably, the use of 2P-SBA-15-PdCl2 (10 mol%) as the catalyst also provided a good yield of 74% (entry 16). The use of 5 mol% 2P-SBA-15-Pd(0) produced the target product 3a in only 63% yield (entry 17), but increasing the palladium loading of the catalyst to 15 mol% failed to improve the yield of 3a significantly (entry 18). When a combination of PdCl2 (10 mol%) with DPPP (10 mol%) was used as the catalytic system, the desired product 3a could also be isolated in 78% yield (entry19), showing that 2P-SBA-15-Pd(0) displays a comparable catalytic activity to its homogeneous analogue. Finally, bromobenzene was tested as the substrate and the target product 3a was obtained in 67% isolated yield (entry 20); however, chlorobenzene was not reactive under the present catalytic system due to its low reactivity (entry 21). Thus, the best result was achieved by the use of 10 mol% 2P-SBA-15-Pd(0) as catalyst and KOtBu as base in toluene at 100 °C for 20 h (entry 3).
a Reaction conditions: 1a (0.5 mmol), 2a (0.7 mmol in pentane), tert-butyl isocyanide (1.5 mmol), 2P-SBA-15-Pd(0) (0.05 mmol, 10 mol%), base (0.65 mmol), solvent (2.0 mL), 100 °C, Ar, 20 h, then 1 M HCl, 1 h.
b Isolated yield.
c tert-butyl isocyanide (1.0 mmol) was used.
d 2P-SiO2-Pd(0) (0.05 mmol, 10 mol%) was used as catalyst.
e 2P-SBA-15-PdCl2 (0.05 mmol, 10 mol%) was used as catalyst.
f 2P-SBA-15-Pd(0) (0.025 mmol, 5 mol%) was used.
g 2P-SBA-15-Pd(0) (0.075 mmol, 15 mol%) was used.
h Reaction was carried out with PdCl2 (10 mol%) and DPPP (10 mol%). DPPP = 1,3-bis(diphenylphosphino)propane.
i Bromobenzene instead of 1a was used.
j Chlorobenzene instead of 1a was used.
With the optimized reaction conditions in hand, we next investigated the scope of this heterogeneous palladium-catalyzed carbonylative coupling of aryl halides and organoaluminum reagents with tert-butyl isocyanide as the CO source. Firstly, we examined the scope of aryl iodides (Table [2]). A wide array of aryl iodides bearing either an electron-donating or an electron-withdrawing substituent underwent the carbonylative coupling smoothly to give the corresponding diketones 3b–j in good to excellent yields. The electronic nature of substituents on the benzene ring had a limited influence on this heterogeneous carbonylation, and both strong electron-donating and strong electron-withdrawing groups were well tolerated. Rigid 4-iodobiphenyl (1k) and bulky 1-iodonaphthalene (1l) were compatible with the standard conditions and gave the desired diketones 3k and 3l in 83 and 95% yield, respectively. Furthermore, the reaction with sterically hindered ortho-substituted aryl iodides 1m–p also proceeded effectively and delivered the expected products 3m–p in 79–93% yields. Notably, a heteroaryl iodide, 3-iodothiophene (1q) was suitable for the reaction and afforded the desired 1-(thiophen-3-yl)propane-1,2-dione 3q in a high yield of 89%. A wide range of functional groups including alkyl, alkoxy, fluoro, chloro, trifluoromethyl, cyano, and ester were tolerated well in the reaction.
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a Reaction conditions: 1 (0.5 mmol), 2a (0.7 mmol in pentane), tert-butyl isocyanide (1.5 mmol), 2P-SBA-15-Pd(0) (0.05 mmol, 10 mol%), KOtBu (0.65 mmol), toluene (2.0 mL), 100 °C, Ar, 20 h, then 1 M HCl, 1 h.
b Isolated yield.
Gratifyingly, aryl bromides can also be utilized as the substrates in this heterogeneous palladium-catalyzed carbonylative coupling reaction. As shown in Table [3], both electron-rich and electron-deficient aryl bromides 4b–j could undergo heterogeneous carbonylative coupling smoothly with AlMe3 under the optimized conditions for aryl iodides and furnished the desired 1,2-diketones 3b, 3r–t, 3e, and 3g–j in good yields of 65–81%. A wide array of functional groups with varied electronic properties were tolerated well. Additionally, the reaction with bulky 2-bromonaphthalene (4k) also worked well, thus delivering the target product 3u in 67% yield. Sterically hindered ortho-substituted aryl bromides 4l–n were well tolerated, producing the expected products 3m–o in 72–81% yields. A heteroaryl bromide, 3-bromothiophene 4o was also a suitable coupling partner, giving the desired 1,2-diketone 3q in good yield.
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a Reaction conditions: 4 (0.5 mmol), 2a (0.7 mmol in pentane), tert-butyl isocyanide (1.5 mmol), 2P-SBA-15-Pd(0) (0.05 mmol, 10 mol%), KOtBu (0.65 mmol), toluene (2.0 mL), 100 °C, Ar, 20 h, then 1 M HCl, 1 h.
b Isolated yield.
Next, different organoaluminum compounds were examined as coupling partners in this heterogeneous carbonylation reaction (Table [4]). Tributylaluminum (2b) and triisobutylaluminum (2c) showed a similar reactivity to AlMe3 and the reactions with iodobenzene (1a) proceeded smoothly to produce the corresponding 1,2-diketones 3v and 3w in 76 and 75% yields, respectively. Triphenylaluminum (2d) as a representative triarylaluminum reagent was also a suitable coupling partner and delivered the desired product 3x in 77% yield. In addition, triisobutylaluminum (2c) underwent carbonylative coupling effectively with diverse electron-rich or electron-deficient aryl iodides to afford the corresponding products 3y–e′ in 64–79% yields. The reactions of heteroaryl iodides with 2c also worked well, thus providing the expected target products 3f′–g′ in 75–84% yields. Similarly, the reactions of triphenylaluminum (2d) with different aryl iodides proceeded smoothly to give the corresponding benzil derivatives 3h′–k′ in 69–78% yields. However, when PhB(OH)2 or PhSi(OMe)3 instead of 2d was used as the coupling partner under the standard conditions, only a trace of the target product was detected.
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a Reaction conditions: 1 (0.5 mmol), 2 (0.7 mmol in pentane), tert-butyl isocyanide (1.5 mmol), 2P-SBA-15-Pd(0) (0.05 mmol, 10 mol%), KOtBu (0.65 mmol), toluene (2.0 mL), 100 °C, Ar, 20 h, then 1 M HCl, 1 h.
b Isolated yield.
To confirm that the observed catalysis arises from the heterogeneous 2P-SBA-15-Pd(0) catalyst and not a leached palladium species in solution, we performed a hot filtration experiment.[25] We focused on the carbonylation reaction of iodobenzene (1a) and trimethylaluminum (2a) under the standard conditions. We removed the catalyst from the reaction mixture by filtration after 4 h of reaction time and the filtrate was allowed to react further for another 16 h. The catalyst filtration was performed at the reaction temperature (100 °C) in order to avoid possible recoordination or precipitation of soluble palladium upon cooling. In this case, no significant increase in conversion of 1a was observed, indicating that the soluble Pd species leached from 2P-SBA-15-Pd(0) are not responsible for the observed activity. It was also verified by ICP-AES analysis that no Pd species could be detected in the filtrate. These results indicate that the bidentate phosphine palladium complex remains on the support at elevated temperatures during the reaction and the observed carbonylative coupling was intrinsically heterogeneous.
A plausible mechanism for the heterogeneous palladium-catalyzed carbonylative coupling of aryl halides and organoaluminum reagents using tert-butyl isocyanide as CO equivalent is illustrated in Scheme [3]. Oxidative addition of Ar-X (1) to the 2P-SBA-15-Pd(0) complex provides the SBA-15-bound arylpalladium(II) complex A, which undergoes coordination and insertion of isocyanide to give the SBA-15-bound palladium(II) complex C. After the coordination of a second molecule of isocyanide, complex D is formed. The latter is subjected to transmetalation with AlR3 (2) and subsequent insertion of isocyanide to generate the SBA-15-bound palladium(II) intermediate E. Finally, intermediate E undergoes a reductive elimination to form the diimine F, which can yield the final 1,2-diketone product (3) after hydrolysis and meanwhile regenerate the 2P-SBA-15-Pd(0) complex for the next catalytic cycle.
For the practical application of a heterogeneous precious-metal catalyst system, its ease of separation, recoverability, and reusability are important factors that need to be evaluated. The 2P-SBA-15-Pd(0) complex can be easily separated and recovered by a simple centrifugation of the reaction mixture. We next examined the recyclability of this heterogenized palladium(0) catalyst in the carbonylative coupling reaction of 4-iodotoluene (1b) with AlMe3. After carrying out the reaction for 20 h, the catalyst was separated by simple centrifugation and washed with distilled water, DMF, and acetone. After drying at 100 °C in vacuo for 1 h, it could be reused directly without further purification. The recovered palladium catalyst was used in the next cycle, and almost constant catalytic efficiency was observed for eight successive cycles (Figure [1]). In addition, the Pd leaching in the heterogenized palladium catalyst was also evaluated by ICP-AES analysis. The palladium content of the catalyst recovered after the eighth reaction cycle was found to be 0.48 mmol/g, indicating that only 2.1% of palladium had been lost from the SBA-15 support.
In conclusion, we have developed a novel, efficient, and practical procedure for the synthesis of 1,2-diketones through heterogeneous palladium(0)-catalyzed carbonylative coupling of aryl halides and organoaluminum compounds using tert-butyl isocyanide as the CO source. The reaction proceeds smoothly in toluene at 100 °C with KOtBu as base by using 10 mol% of an SBA-15-anchored bidentate phosphine palladium(0) complex [2P-SBA-15-Pd(0)] as the catalyst, yielding a wide array of 1,2-diketones in good to excellent yields. Both alkyl- and arylaluminum compounds were suitable substrates for this transformation and a wide range of functional groups on aryl iodides or bromides were well tolerated. Furthermore, this supported palladium(0) catalyst can be conveniently prepared from commercially readily available materials, and reused at least seven times without any significant drop in its catalytic efficiency, which makes the current method economically and environmentally more acceptable.
All starting materials and mesoporous SBA-15 were purchased from commercial suppliers and used without further purification prior to use. Aryl iodides 1, aryl bromides 4, trimethylaluminum 2a, and tri(isobutyl)aluminum 2c were commercially available, and organoaluminum reagents 2b and 2d were prepared from aluminum trichloride and Grignard or organolithium reagents according to a reported procedure.[18] Toluene, dioxane, and THF were dried over sodium and distilled. MeCN and DMF were dried with CaH2 and distilled prior to use. All reactions were performed under an atmosphere of argon in oven-dried glassware. The products were purified by column chromatography on silica gel. Mixtures of petroleum ether and EtOAc were generally used as eluent. 1H and 13C NMR spectra were recorded at 400 or 100 MHz with CDCl3 as the solvent and TMS as an internal standard. Chemical shifts are given as δ values relative to TMS. HRMS spectra were recorded with a Q-Tof spectrometer with Micromass MS software using electrospray ionization (ESI). Melting points are uncorrected. The palladium content of the catalyst was measured by ICP-AES analysis.
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Preparation of the 2P-SBA-15-Pd(0) Complex
A mixture of (EtO)3Si(CH2)3NH2 (1.45 g, 6.5 mmol) and mesoporous SBA-15 material (2.0 g) in anhydrous toluene (120 mL) was stirred at 110 °C under argon for 48 h. After cooling to r.t., the product was filtered, followed by washing with toluene (30 mL), and drying at 110 °C in vacuo for 3 h. The resultant powdery solid was stirred with (Me3Si)2NH (4.0 g) at r.t. in anhydrous toluene (100 mL) under argon for 24 h. The product was collected by filtration, washed with acetone (2 × 35 mL), and dried at 90 °C under vacuum for 3 h to afford the aminopropyl-modified mesoporous SBA-15 material (H2N-SBA-15; 2.617 g). The nitrogen content of H2N-SBA-15 was measured to be 1.14 mmol g–1 by elemental analysis.
To a suspension of paraformaldehyde (0.96 g, 32 mmol) in anhydrous toluene (100 mL) was added diphenylphosphine (7.82 g, 42 mmol) under argon. The resulting mixture was stirred at reflux under argon for 3 h, then H2N-SBA-15 (2.0 g, 2.28 mmol NH2) was added at r.t. and the mixture was stirred at reflux for 24 h. After cooling to r.t., the product was filtered, washed with toluene (3 × 30 mL) and dried at 80 °C in vacuo for 2 h to give the bidentate phosphino-functionalized SBA-15 material (2P-SBA-15; 2.317 g). The phosphorus content of 2P-SBA-15 was measured to be 1.28 mmol g–1 by ICP-AES. A mixture of PdCl2 (107 mg, 0.60 mmol) and 2P-SBA-15 (1.0 g) in acetone (40 mL) was stirred at 60 °C under argon for 72 h. The product was filtered, followed by washing with acetone (2 × 25 mL), and drying at 70 °C in vacuo for 4 h to provide 2P-SBA-15-PdCl2 (1.034 g) as a pale-yellow solid. The latter was then stirred with hydrazine hydrate (3.5 mL) in EtOH (30 mL) at r.t. for 3 h. The resultant product was filtered, washed with distilled water (2 × 25 mL) and EtOH (2 × 25 mL), and dried at 80 °C in vacuo for 3 h to afford 2P-SBA-15-Pd(0) (1.017 g) as a gray powdery solid with palladium content of 0.49 mmol g–1 based on ICP-AES analysis.
The 2P-SiO2-Pd(0) complex was prepared similarly, by replacement of SBA-15 with fumed silica (SiO2, 2.0 g). The palladium content of 2P-SiO2-Pd(0) was found to be 0.42 mmol g–1 based on ICP-AES analysis.
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Heterogeneous Palladium(0)-Catalyzed Carbonylative Coupling of Aryl Halides and Organoaluminum Compounds using tert-Butyl Isocyanide as CO Equivalent; General Procedure
To an 8-mL pressure tube equipped with a stir bar was added 2P-SBA-15-Pd(0) (112 mg, 0.05 mmol) under argon. Then degassed toluene (2 mL) was added, followed by addition of tert-butylisocyanide (1.5 mmol), aryl halide (0.5 mmol, 1.0 equiv), and organoaluminium reagent (0.7 mmol). The reaction mixture was stirred for 5 min at r.t., then KOtBu (0.65 mmol, 1.3 equiv) was added and the reaction mixture was heated to 100 °C and then stirred for 20 h. After cooling to r.t., the palladium catalyst was separated by a simple centrifugation of the reaction mixture and washed with distilled water (2 × 5 mL), DMF (5 mL), and acetone (2 × 5 mL). After drying at 100 °C in vacuo for 1 h, the recovered catalyst can be reused directly in the next run. Then THF (2 mL) and 1 M HCl (2 mL) were added to the resultant reaction solution, and the mixture was stirred at r.t. for 1 h. The mixture was diluted with water (10 mL) and extracted with EtOAc (3 × 10 mL). The organic extracts were dried over MgSO4 and concentrated under reduced pressure. The residue was then purified by flash column chromatography on silica gel (petroleum ether/EtOAc, 25:1) to afford the desired 1,2-diketone 3.
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1-Phenylpropane-1,2-dione (3a)[18]
Yield: 58.5 mg (79%); pale-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 8.03–8.00 (m, 2 H), 7.64 (t, J = 7.4 Hz, 1 H), 7.50 (t, J = 7.8 Hz, 2 H), 2.53 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 200.5, 191.4, 134.6, 131.8, 130.3, 128.8, 26.4.
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1-(p-Tolyl)propane-1,2-dione (3b)[18]
Yield: 76.2 mg (94%); pale-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 7.91 (d, J = 8.4 Hz, 2 H), 7.30 (d, J = 8.0 Hz, 2 H), 2.51 (s, 3 H), 2.43 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 200.9, 191.2, 145.9, 130.4, 129.6, 129.3, 26.4, 21.9.
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1-(4-Methoxyphenyl)propane-1,2-dione (3c)[18]
Yield: 81.9 mg (92%); pale-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 8.01 (d, J = 8.8 Hz, 2 H), 6.96 (d, J = 8.8 Hz, 2 H), 3.88 (s, 3 H), 2.50 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 201.0, 190.0, 164.8, 132.8, 124.8, 114.2, 55.6, 26.4.
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1-(4-(Trifluoromethoxy)phenyl)propane-1,2-dione (3d)
Yield: 95.2 mg (82%); pale-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 8.12 (d, J = 9.2 Hz, 2 H), 7.32 (d, J = 8.4 Hz, 2 H), 2.54 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 199.9, 189.2, 153.8, 132.7, 130.2, 120.6, 120.4 (q, J = 257.9 Hz), 26.3.
19F NMR (376 MHz, CDCl3): δ = –57.5 (s, 3 F).
HRMS (ESI): m/z [M + Na]+ calcd for C10H7F3NaO3: 255.0239; found: 255.0242.
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1-(Benzo[d][1,3]dioxol-5-yl)propane-1,2-dione (3e)[18]
Yield: 92.2 mg (96%); pale-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 7.63 (d, J = 8.0 Hz, 1 H), 7.48 (s, 1 H), 6.88 (d, J = 8.0 Hz, 1 H), 6.07 (s, 2 H), 2.49 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 200.8, 189.7, 153.3, 148.5, 128.0, 126.4, 109.0, 108.3, 102.1, 26.6.
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1-(4-Fluorophenyl)propane-1,2-dione (3f)[26]
Yield: 66.4 mg (80%); pale-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 8.11–8.07 (m, 2 H), 7.17 (t, J = 8.6 Hz, 2 H), 2.52 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 200.1, 189.3, 166.7 (d, J = 256.3 Hz), 133.3 (d, J = 9.6 Hz), 128.3 (d, J = 2.9 Hz), 116.2 (d, J = 21.9 Hz), 26.3.
19F NMR (376 MHz, CDCl3): δ = –104.1 (s, 1 F).
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1-(4-Chlorophenyl)propane-1,2-dione (3g)[18]
Yield: 77.6 mg (85%); pale-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 7.99 (d, J = 8.8 Hz, 2 H), 7.47 (d, J = 8.4 Hz, 2 H), 2.53 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 199.8, 189.5, 141.3, 131.8, 130.2, 129.2, 26.2.
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1-(4-(Trifluoromethyl)phenyl)propane-1,2-dione (3h)[26]
Yield: 84.3 mg (78%); pale-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 8.16 (d, J = 8.0 Hz, 2 H), 7.76 (d, J = 8.4 Hz, 2 H), 2.56 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 199.3, 189.5, 135.7 (q, J = 32.7 Hz), 134.8, 130.9, 125.9 (q, J = 3.7 Hz), 123.5 (q, J = 271.2 Hz), 26.2.
19F NMR (376 MHz, CDCl3): δ = –63.4 (s, 3 F).
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4-(2-Oxopropanoyl)benzonitrile (3i)
Yield: 68.4 mg (79%); pale-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 8.16 (d, J = 8.4 Hz, 2 H), 7.80 (d, J = 8.4 Hz, 2 H), 2.56 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 198.7, 188.7, 135.1, 132.5, 130.8, 117.7, 117.5, 26.0.
HRMS (ESI): m/z [M + H]+ calcd for C10H8NO2: 174.0550; found: 174.0555.
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Methyl 4-(2-Oxopropanoyl)benzoate (3j)[26]
Yield: 86.6 mg (84%); white solid; mp 137–138 °C.
1H NMR (400 MHz, CDCl3): δ = 8.14 (d, J = 8.4 Hz, 2 H), 8.10–8.07 (m, 2 H), 3.96 (s, 3 H), 2.55 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 199.6, 190.2, 166.0, 135.1, 135.0, 130.3, 129.8, 52.6, 26.2.
#
1-([1,1′-Biphenyl]-4-yl)propane-1,2-dione (3k)[26]
Yield: 93.1 mg (83%); white solid; mp 93–94 °C.
1H NMR (400 MHz, CDCl3): δ = 8.09 (d, J = 8.4 Hz, 2 H), 7.71 (d, J = 8.4 Hz, 2 H), 7.62 (d, J = 7.2 Hz, 2 H), 7.47 (t, J = 7.4 Hz, 2 H), 7.41 (t, J = 7.2 Hz, 1 H), 2.55 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 200.5, 190.8, 147.3, 139.6, 130.9, 130.5, 129.0, 128.6, 127.5, 127.3, 26.3.
#
1-(Naphthalen-1-yl)propane-1,2-dione (3l)[18]
Yield: 94.1 mg (95%); pale-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 8.89 (d, J = 8.4 Hz, 1 H), 8.08 (d, J = 8.0 Hz, 1 H), 7.92–7.89 (m, 2 H), 7.66 (t, J = 7.6 Hz, 1 H), 7.57 (t, J = 7.4 Hz, 1 H), 7.51 (t, J = 7.8 Hz, 1 H), 2.60 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 201.0, 194.5, 135.3, 134.1, 133.5, 131.2, 128.9, 128.8, 127.9, 126.9, 125.6, 124.2, 26.4.
#
1-(o-Tolyl)propane-1,2-dione (3m)[18]
Yield: 75.4 mg (93%); light-yellow solid; mp 87–88 °C.
1H NMR (400 MHz, CDCl3): δ = 7.61 (d, J = 8.0 Hz, 1 H), 7.49–7.45 (m, 1 H), 7.32–7.27 (m, 2 H), 2.55 (s, 3 H), 2.53 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 200.9, 194.6, 140.8, 133.2, 132.2, 132.0, 131.2, 125.7, 26.0, 21.4.
#
1-(2-Methoxyphenyl)propane-1,2-dione (3n)[18]
Yield: 79.3 mg (89%); pale-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 7.81 (dd, J = 7.6, 1.6 Hz, 1 H), 7.60–7.55 (m, 1 H), 7.08 (t, J = 7.4 Hz, 1 H), 6.98 (d, J = 8.4 Hz, 1 H), 3.84 (s, 3 H), 2.44 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 200.7, 194.7, 160.0, 135.9, 130.5, 123.3, 121.6, 112.1, 55.9, 24.8.
#
1-(2-Fluorophenyl)propane-1,2-dione (3o)[26]
Yield: 67.2 mg (81%); pale-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 7.87–7.82 (m, 1 H), 7.65–7.59 (m, 1 H), 7.32–7.28 (m, 1 H), 7.18–7.13 (m, 1 H), 2.52 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 199.4, 191.3, 162.6 (d, J = 254.6 Hz), 136.3 (d, J = 9.0 Hz), 131.1 (d, J = 2.1 Hz), 125.0 (d, J = 3.2 Hz), 121.9 (d, J = 12.0 Hz), 116.6 (d, J = 21.5 Hz), 25.0.
19F NMR (376 MHz, CDCl3): δ = –108.8 (s, 1 F).
#
1-(2-Chlorophenyl)propane-1,2-dione (3p)[26]
Yield: 72.1 mg (79%); pale-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 7.65 (dd, J = 7.6, 1.6 Hz, 1 H), 7.53–7.48 (m, 1 H), 7.44–7.37 (m, 2 H), 2.57 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 198.6, 193.2, 134.1, 134.0, 133.3, 131.4, 130.2, 127.4, 25.0.
#
1-(Thiophen-3-yl)propane-1,2-dione (3q)[27]
Yield: 68.6 mg (89%); pale-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 8.53 (d, J = 1.2 Hz, 1 H), 7.68 (d, J = 4.4 Hz, 1 H), 7.36–7.33 (m, 1 H), 2.50 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 199.5, 182.8, 137.8, 136.2, 128.1, 126.4, 25.6.
#
1-(m-Tolyl)propane-1,2-dione (3r)[18]
Yield: 57.6 mg (71%); pale-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 7.82–7.75 (m, 2 H), 7.45 (d, J = 7.2 Hz, 1 H), 7.41–7.34 (m, 1 H), 2.51 (s, 3 H), 2.42 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 200.8, 191.9, 138.8, 135.5, 131.7, 130.6, 128.7, 127.6, 26.5, 21.3.
#
1-(4-(tert-Butyl)phenyl)propane-1,2-dione (3s)[18]
Yield: 82.7 mg (81%); pale-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 7.95 (d, J = 8.8 Hz, 2 H), 7.52 (d, J = 8.4 Hz, 2 H), 2.51 (s, 3 H), 1.34 (s, 9 H).
13C NMR (100 MHz, CDCl3): δ = 200.9, 191.2, 158.7, 130.3, 129.2, 125.9, 35.3, 31.0, 26.4.
#
1-(3-Methoxyphenyl)propane-1,2-dione (3t)[28]
Yield: 68.6 mg (77%); pale-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 7.57 (d, J = 7.6 Hz, 1 H), 7.53 (s, 1 H), 7.40 (t, J = 7.8 Hz, 1 H), 7.19 (dd, J = 8.2, 1.8 Hz, 1 H), 3.86 (s, 3 H), 2.52 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 200.5, 191.4, 159.9, 133.0, 129.9, 123.3, 121.5, 113.6, 55.5, 26.4.
#
1-(Naphthalen-2-yl)propane-1,2-dione (3u)[18]
Yield: 66.4 mg (67%); pale-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 8.57 (s, 1 H), 8.04 (dd, J = 8.6, 1.4 Hz, 1 H), 7.97–7.86 (m, 3 H), 7.66–7.62 (m, 1 H), 7.57 (t, J = 7.6 Hz, 1 H), 2.59 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 200.7, 191.4, 136.2, 133.7, 132.4, 130.0, 129.4, 129.0, 128.9, 127.9, 127.1, 124.3, 26.5.
#
1-Phenylhexane-1,2-dione (3v)[18]
Yield: 72.2 mg (76%); pale-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 7.99–7.96 (m, 2 H), 7.66–7.61 (m, 1 H), 7.49 (t, J = 7.6 Hz, 2 H), 2.88 (t, J = 7.4 Hz, 2 H), 1.71–1.64 (m, 2 H), 1.44–1.38 (m, 2 H), 0.94 (t, J = 7.4 Hz, 3 H).
13C NMR (100 MHz, CDCl3): δ = 203.6, 192.7, 134.7, 132.1, 130.3, 128.9, 38.6, 25.0, 22.4, 13.9.
#
4-Methyl-1-phenylpentane-1,2-dione (3w)[18]
Yield: 71.3 mg (75%); pale-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 8.00–7.97 (m, 2 H), 7.66–7.62 (m, 1 H), 7.50 (t, J = 7.6 Hz, 2 H), 2.77 (d, J = 6.8 Hz, 2 H), 2.30–2.21 (m, 1 H), 1.01 (d, J = 6.8 Hz, 6 H).
13C NMR (100 MHz, CDCl3): δ = 203.3, 192.6, 134.7, 132.1, 130.3, 129.0, 47.6, 24.2, 22.8.
#
Benzil (3x)[18]
Yield: 80.9 mg (77%); white solid; mp 95–96 °C.
1H NMR (400 MHz, CDCl3): δ = 7.99–7.96 (m, 4 H), 7.66 (t, J = 7.4 Hz, 2 H), 7.51 (t, J = 7.8 Hz, 4 H).
13C NMR (100 MHz, CDCl3): δ = 194.6, 134.9, 133.0, 129.9, 129.0.
#
1-(4-(tert-Butyl)phenyl)-4-methylpentane-1,2-dione (3y)
Yield: 97.3 mg (79%); pale-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 7.93 (d, J = 8.4 Hz, 2 H), 7.51 (d, J = 8.4 Hz, 2 H), 2.76 (d, J = 6.8 Hz, 2 H), 2.30–2.22 (m, 1 H), 1.34 (s, 9 H), 1.01 (d, J = 6.8 Hz, 6 H).
13C NMR (100 MHz, CDCl3): δ = 203.6, 192.3, 158.7, 130.3, 129.5, 126.0, 47.6, 35.4, 31.1, 24.2, 22.8.
HRMS (ESI): m/z [M + Na]+ calcd for C16H22NaO2: 269.1512; found: 269.1510.
#
1-(4-Methoxyphenyl)-4-methylpentane-1,2-dione (3z)[28]
Yield: 81.5 mg (74%); pale-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 7.98 (dd, J = 7.2, 2.0 Hz, 2 H), 6.96 (dd, J = 7.2, 2.0 Hz, 2 H), 3.89 (s, 3 H), 2.75 (d, J = 6.8 Hz, 2 H), 2.31–2.21 (m, 1 H), 1.00 (d, J = 6.4 Hz, 6 H).
13C NMR (100 MHz, CDCl3): δ = 203.8, 191.2, 164.9, 132.8, 125.0, 114.3, 55.7, 47.7, 24.2, 22.8.
#
1-(3-Methoxyphenyl)-4-methylpentane-1,2-dione (3a′)
Yield: 83.7 mg (76%); pale-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 7.55–7.50 (m, 2 H), 7.40 (t, J = 8.0 Hz, 1 H), 7.21–7.17 (m, 1 H), 3.86 (s, 3 H), 2.76 (d, J = 6.8 Hz, 2 H), 2.32–2.22 (m, 1 H), 1.01 (d, J = 6.8 Hz, 6 H).
13C NMR (100 MHz, CDCl3): δ = 203.3, 192.6, 160.1, 133.3, 130.0, 123.3, 121.6, 113.6, 55.6, 47.7, 24.2, 22.8.
HRMS (ESI): m/z [M + Na]+ calcd for C13H16NaO3: 243.0992; found: 243.0987.
#
1-(4-Fluorophenyl)-4-methylpentane-1,2-dione (3b′)
Yield: 70.7 mg (68%); pale-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 8.08–8.03 (m, 2 H), 7.17 (td, J = 8.6, 1.8 Hz, 2 H), 2.77 (d, J = 6.8 Hz, 2 H), 2.31–2.21 (m, 1 H), 1.01 (d, J = 6.4 Hz, 6 H).
13C NMR (100 MHz, CDCl3): δ = 202.9, 190.5, 166.8 (d, J = 256.2 Hz), 133.2 (d, J = 9.6 Hz), 128.6 (d, J = 3.0 Hz), 116.3 (d, J = 22.0 Hz), 47.5, 24.3, 22.8.
19F NMR (376 MHz, CDCl3): δ = –104.4 (s, 1 F).
HRMS (ESI): m/z [M + Na]+ calcd for C12H13FNaO2: 231.0792; found: 231.0793.
#
1-(3-Fluorophenyl)-4-methylpentane-1,2-dione (3c′)
Yield: 66.6 mg (64%); pale-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 7.79 (d, J = 7.6 Hz, 1 H), 7.73–7.69 (m, 1 H), 7.51–7.45 (m, 1 H), 7.37–7.31 (m, 1 H), 2.77 (d, J = 6.8 Hz, 2 H), 2.31–2.21 (m, 1 H), 1.01 (d, J = 6.8 Hz, 6 H).
13C NMR (100 MHz, CDCl3): δ = 202.4, 190.8, 162.9 (d, J = 247.3 Hz), 134.1 (d, J = 6.4 Hz), 130.7 (d, J = 7.5 Hz), 126.3 (d, J = 3.0 Hz), 121.7 (d, J = 21.2 Hz), 116.8 (d, J = 22.6 Hz), 47.5, 24.3, 22.8.
19F NMR (376 MHz, CDCl3): δ = –112.2 (s, 1 F).
HRMS (ESI): m/z [M + Na]+ calcd for C12H13FNaO2: 231.0792; found: 231.0790.
#
Methyl 4-(4-Methyl-2-oxopentanoyl)benzoate (3d′)
Yield: 85.6 mg (69%); pale-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 8.15 (d, J = 8.4 Hz, 2 H), 8.06 (d, J = 8.8 Hz, 2 H), 3.96 (s, 3 H), 2.79 (d, J = 6.8 Hz, 2 H), 2.30–2.22 (m, 1 H), 1.02 (d, J = 6.8 Hz, 6 H).
13C NMR (100 MHz, CDCl3): δ = 202.3, 191.4, 166.1, 135.4, 135.1, 130.2, 130.0, 52.7, 47.4, 24.3, 22.8.
HRMS (ESI): m/z [M + Na]+ calcd for C14H16NaO4: 271.0941; found: 271.0944.
#
4-(4-Methyl-2-oxopentanoyl)benzonitrile (3e′)
Yield: 77.4 mg (72%); pale-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 8.12 (d, J = 8.8 Hz, 2 H), 7.80 (d, J = 8.8 Hz, 2 H), 2.80 (d, J = 6.8 Hz, 2 H), 2.31–2.22 (m, 1 H), 1.01 (d, J = 6.8 Hz, 6 H).
13C NMR (100 MHz, CDCl3): δ = 201.4, 189.7, 135.2, 132.5, 130.6, 117.7, 117.5, 47.1, 24.2, 22.6.
HRMS (ESI): m/z [M + Na]+ calcd for C13H13NNaO2: 238.0838; found: 238.0845.
#
4-Methyl-1-(pyridin-3-yl)pentane-1,2-dione (3f′)[29]
Yield: 80.3 mg (84%); pale-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 9.22 (t, J = 1.0 Hz, 1 H), 8.83 (dd, J = 4.8, 1.6 Hz, 1 H), 8.34–8.31 (m, 1 H), 7.47–7.43 (m, 1 H), 2.81 (d, J = 7.2 Hz, 2 H), 2.30–2.23 (m, 1 H), 1.02 (d, J = 6.8 Hz, 6 H).
13C NMR (100 MHz, CDCl3): δ = 201.3, 190.0, 154.3, 151.6, 137.4, 127.9, 123.7, 46.8, 24.2, 22.6.
#
4-Methyl-1-(thiophen-3-yl)pentane-1,2-dione (3g′)
Yield: 73.6 mg (75%); pale-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 8.48 (dd, J = 2.8, 1.2 Hz, 1 H), 7.67 (dd, J = 5.0, 1.0 Hz, 1 H), 7.36 (dd, J = 5.0, 3.0 Hz, 1 H), 2.78 (d, J = 6.8 Hz, 2 H), 2.26–2.17 (m, 1 H), 0.99 (d, J = 6.8 Hz, 6 H).
13C NMR (100 MHz, CDCl3): δ = 202.1, 184.0, 137.6, 136.7, 128.1, 126.6, 46.7, 24.4, 22.8.
HRMS (ESI): m/z [M + H]+ calcd for C10H13O2S: 197.0631; found: 197.0627.
#
1-Phenyl-2-(p-tolyl)ethane-1,2-dione (3h′)[30]
Yield: 82.9 mg (74%); pale-yellow solid; mp 95–96 °C.
1H NMR (400 MHz, CDCl3): δ = 7.96 (d, J = 7.6 Hz, 2 H), 7.87 (d, J = 8.0 Hz, 2 H), 7.64 (t, J = 7.4 Hz, 1 H), 7.50 (t, J = 7.8 Hz, 2 H), 7.30 (d, J = 8.0 Hz, 2 H), 2.43 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 194.8, 194.3, 146.2, 134.8, 133.1, 130.6, 130.0, 129.8, 129.7, 129.0, 21.9.
#
1-(4-Methoxyphenyl)-2-phenylethane-1,2-dione (3i′)[30]
Yield: 93.6 mg (78%); pale-yellow solid; mp 61–62 °C.
1H NMR (400 MHz, CDCl3): δ = 7.97–7.92 (m, 4 H), 7.63 (t, J = 7.4 Hz, 1 H), 7.48 (t, J = 7.8 Hz, 2 H), 6.96 (d, J = 9.2 Hz, 2 H), 3.86 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 194.9, 193.2, 165.0, 134.7, 133.2, 132.3, 129.8, 128.9, 126.1, 114.4, 55.6.
#
Methyl 4-(2-oxo-2-phenylacetyl)benzoate (3j′)[30]
Yield: 92.5 mg (69%); pale-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 8.15–8.12 (m, 2 H), 8.02 (d, J = 8.4 Hz, 2 H), 7.97–7.94 (m, 2 H), 7.67–7.62 (m, 1 H), 7.50 (t, J = 7.8 Hz, 2 H), 3.93 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 193.8, 193.6, 165.8, 136.1, 135.3, 135.1, 132.7, 130.1, 129.9, 129.7, 129.1, 52.6.
#
1-(4-Nitrophenyl)-2-phenylethane-1,2-dione (3k′)[30]
Yield: 95.7 mg (75%); pale-yellow solid; mp 126–127 °C.
1H NMR (400 MHz, CDCl3): δ = 8.36 (d, J = 9.2 Hz, 2 H), 8.17 (d, J = 8.8 Hz, 2 H), 8.01–7.98 (m, 2 H), 7.71 (t, J = 7.4 Hz, 1 H), 7.55 (t, J = 7.8 Hz, 2 H).
13C NMR (100 MHz, CDCl3): δ = 192.8, 192.1, 151.2, 137.4, 135.4, 132.4, 130.9, 130.1, 129.2, 124.1.
#
#
Conflict of Interest
The authors declare no conflict of interest.
Supporting Information
- Supporting information for this article is available online at https://doi-org.accesdistant.sorbonne-universite.fr/10.1055/s-0040-1720121.
- Supporting Information
-
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- 24e Xu Z, Huang B, Zhou Z, Cai M. Synthesis 2020; 52: 581
- 24f Zhou Y, Zhou Z, Liu S, Cai M. Mol. Catal. 2022; 526: 112404
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- 28 Liu Y, Yun X, Zhang-Negrerie D, Huang J, Du Y, Zhang K. Synthesis 2011; 2984
- 29 Wehrle RJ, Rosen A, Nguyen TV, Koons K, Jump E, Bullard M, Wehrle N, Stockfish A, Hare PM, Atesin A, Atesin TA, Ma L. ACS Omega 2022; 7: 26650
- 30 Zeng J, Li J, Huang B, Li J, Cai M. J. Organomet. Chem. 2022; 976: 122435
Corresponding Authors
Publication History
Received: 13 April 2024
Accepted after revision: 21 May 2024
Article published online:
03 June 2024
© 2024. Thieme. All rights reserved
Georg Thieme Verlag KG
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