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DOI: 10.1055/s-0035-1560372
TfOH-Catalyzed Reaction of Bispropargyl Alcohols with 1,3-Dicarbonyl Compounds
Publication History
Received: 30 July 2015
Accepted after revision: 15 October 2015
Publication Date:
17 November 2015 (online)
Abstract
A transition-metal-free efficient method for the preparation of 1,2,3-trisubstituted benzenes from bispropargyl alcohols and 1,3-dicarbonyl compounds has been developed. The reaction of bispropargyl alcohol with 1,3-dicarbonyl compound proceeds through [3,3]-rearrangement, 6π-electrocyclization, and unexpected Csp3−Csp2 regioselective σ-bond cleavage processes.
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Key words
bispropargyl alcohols - 1,3-dicarbonyl componds - [3,3]-rearrangement - C−C α′-moiety cleavage - 6π-electrocyclization process - 1,2,3-trisubstituted benzenesCarbon−carbon bond formation and cleavage (activation) have attracted considerable attention in recent years due to their importance in fundamental scientific research and practical applications in organic synthesis.[1] Indeed, C−C bond cleavage of carbonyl compounds is frequently observed in a number of well-known reactions, such as Baeyer–Villiger,[2] haloform,[3] and Haller–Bauer[4] reactions. As inexpensive and easily accessible starting materials, 1,3-diketones have been widely used as starting materials in organic synthesis.[5] Over the past few years, various cascade reactions of 1,3-dicarbonyl compounds involving C−C σ-bond cleavage have been developed[6] (Scheme [1]). However, reports about α′-moiety cleavage of unactivated 1,3-dicarbonyls are rare compared to those about conventional activated carbonyls, such as anhydrides,[7a] chloroformates,[7b] and aldehydes,[7c] [d] which are used as precursors of acyl radical. As a continuation of our efforts to the study of 1,3-dicarbonyls,[8] we explored the reaction of 1,3-dicarbonyls with bispropargyl alcohols to create functionalized ring structures. Herein, we report a mild and efficient transition-metal-free method for the synthesis of 1,2,3-trisubstituted benzenes from bispropargyl alcohols and α′-moiety of 1,3-dicarbonyls, which are useful substrates for the study of Sil-PImC18-MO phase,[9] d2-SS-RTP,[10] and photoamination,[11] and are effective quenchers of DCA fluorescence,[12] via the [3,3]-rearrangement, 6π-electrocyclization, and unexpected Csp3−Csp2 regioselective σ-bond cleavage processes.
To identify the suitable conditions for the reaction, a series of catalysts and solvents were screened using 1,5-diphenylpenta-1,4-diyn-3-ol (1a) and acetylacetone (2a) as a model system (Table [1]). Initially, the desired product 3aa was isolated in 90% yield in the presence of 10 mol% TfOH in chlorobenzene at 110 °C for two hours (Table [1], entry 1). Screening of the catalysts (TFA, HCl, H2SO4, AcOH, formic acid, H3PO4, DIB, PTSA, oxalic acid, HClO4) (entries 2–11) revealed that 10 mol% of TfOH was optimal to give the annulation product 3aa in 90% yield (entry 1), but no obvious improvement in yield could be observed as the amount of TfOH was increased to 15 mol% (entry 12). Notably, HClO4, which is a typical superacid, did not promote the reaction smoothly even after a longer reaction time (entry 11). The solvent screening indicated that chlorobenzene was the most suitable reaction medium among the investigated solvents (entry 1 vs entries 13–18) while polar solvents, such as DMF, DMSO, 1,4-dioxane, and acetonitrile, were not suitable for this reaction (entries 15–18). Therefore, the optimized reaction conditions are 10 mol% TfOH as the catalyst, chlorobenzene as the solvent, and a reaction temperature of 110 °C.
a Reaction conditions: 1 (0.5 mmol), 2 (0.55 mmol), catalyst (10 mol%), and solvent (2 mL) at 110 °C, 2 h.
b Isolated yield.
c The reaction was carried out in a sealed tube.
d Reaction time: 5 h.
e The reaction was carried out using 15 mol% catalyst.
Having established the optimized reaction conditions, the substrate scopes were subsequently investigated for this transformation. Typical results are presented in Table [2]. Various 1,3-diketones were suitable reaction partners for bispropargyl alcohol 1a to form the substituted benzenes. The reaction of ethyl acetoacetate (2b), 1-phenylbutane-1,3-dione (2c), and heptane-3,5-dione (2e) gave the corresponding substituted benzenes 3aa–ae in 78–90% yields (Table [2], entries 2, 3, and 5). When the EWG group of 1,3-diketone was changed to tosyl, the reaction produced the desired product 3aa in 66% yield (entry 4). To our delight, the ethyl 4-chloro-3-oxobutanoate (2f) reacted smoothly and afforded the desired product 3af albeit in 35% yield (entry 6). Obviously, electron-rich 1,3-diketones provided the desired products in higher yields than electron-poor 1,3-diketones (entries 1 and 5 vs entry 6). Unfortunately, simple ketones such as acetone, acetophenone, and 1-phenylpropan-2-one, could not be applied for this transformation. The aromatic bispropargyl alcohols 1b–f possessing electron-donating groups on the aryl rings provided the desired products 3ba–fa in 70–92% yields (entries 7–12). In addition, the bispropargyl alcohol 1g possessing a methyl at the meta-position of aryl ring (R1 = 3-MeC6H4) also reacted readily to yield the desired product 3ga in 86% yield (entry 13). We also observed that aromatic bispropargyl alcohols 1h,i with an electron-withdrawing group (bromo and fluoro) at the benzene ring gave the corresponding products in moderate yields (entries 14 and 15). Interestingly, 1,5-bis(4-bromophenyl)penta-1,4-diyn-3-ol (1i) afforded the desired product 3ia along with an unexpected product 3ja (only one bromine atom remained) in 60% total yield. Obviously, electron-rich bispropargylic alcohols provided cyclization products in higher yields than electron-poor bispropargylic alcohols, which could be attributed to the electron-withdrawing inductive effects of the halogen substituent at the aryl ring. Unfortunately, the terminal bispropargyl alcohols (R1 = H) and aliphatic bispropargyl alcohols failed to afford the desired products.
To investigate the reaction mechanism, control experiments were performed and the results are presented in Scheme [2]. The condensation of 1,5-diphenylpenta-1,4-diyn-3-ol (1a) with acetylacetone (2a) generated product 5aa in 95% yield in the presence of TfOH (10 mol%) in chlorobenzene at 50 °C for one hour. Subsequently, 5aa undergoes [3,3]-rearrangement/6π-electrocyclization process/ Csp3−Csp2 regioselective σ-bond cleavage to afford 3aa in 92% yield under standard conditions.
a Reaction conditions: 1 (0.5 mmol), 2 (0.55 mmol), TfOH (10 mol%), and PhCl (2 mL) at 110 °C, 2 h.
b Isolated yield.
c Total yield.
On the basis of the above results, a plausible mechanistic description is shown in Scheme [3]. First, the ionization of 1a would lead to bispropargylic cation 4 and the subsequent nucleophilic attack of 2a gives the key intermediate 5aa followed by tautomerization and [3,3]-rearrangement to intermediate 7.[13] [14] In the following process, a tautomerization and 6π-electrocyclization of intermediate 7 produces intermediate 9,[15] followed by its reaction with H2O in the presence of TfOH to generate intermediate 11. Finally, the intermediate 11 proceeds to afford the desired product 3aa and 3-oxobutanoic acid (12). When 2c was used, acetophenone (decarboxylation of 3-oxo-3-phenylpropanoic acid) was detected by HRMS (see Supporting Information). It also confirmed the proposed reaction mechanism.
In conclusion, a novel and efficient TfOH-catalyzed reaction of bispropargyl alcohols with 1,3-diketones has been developed. This transformation provides ready and practical access to 1,2,3-trisubstituted benzenes that would not be easily accessed. To the best of our knowledge, this represents the first report of TfOH-promoted process for the construction of polysubstituted aromatic compounds via the selective Csp3−Csp2 σ-bond cleavage of 1,3-dicarbonyl compounds in a one-pot fashion.
All manipulations were performed under air atmosphere, unless stated otherwise. Column chromatography was performed on silica gel (300–400 mesh). NMR spectra were recorded on a Bruker Avance 500 spectrometer (1H at 500 MHz and 13C at 125 MHz). Mass spectra were recorded on a Gas Chromatograph-Mass Spectrometer (Shimadzu, Japan) equipped with an EI ionization source. High resolution mass spectra were recorded on the Exactive Mass Spectrometer (Thermo Scientific, USA) equipped with an ESI ionization source. All reagents, unless stated otherwise, were of commercial origin and were used without further purification. All reagents were measured and handled in air at r.t. Petroleum ether (PE) used refers to the hydrocarbon mixture with a boiling range of 60–90 °C.
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1,2,3-Trisubstituted Benzenes 3; General Procedure
A reaction mixture of bispropargyl alcohol 1 (0.5 mmol), 1,3-diketone 2 (0.55 mmol), TfOH (10 mol%), and PhCl (2 mL) was placed in a 10 mL flask and stirred at 110 °C in air, monitoring the progress of the reaction periodically by TLC. Upon completion of the reaction, the solvent was removed under vacuum. The crude product was purified by flash column chromatography on silica gel (PE–EtOAc, 20:1 to 10:1) to afford the substituted benzene derivative 3 (Table [2]).
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1,1′:3′,1′′-Terpheny (3aa)[16]
Yield: 103.5 mg (90%); white solid; mp 84–87 °C.
1H NMR (500 MHz, CDCl3): δ = 7.85 (s, 1 H), 7.68 (d, J = 7.8 Hz, 4 H), 7.61 (d, J = 8.1 Hz, 2 H), 7.56–7.52 (m, 1 H), 7.50 (t, J = 7.6 Hz, 4 H), 7.40 (t, J = 7.4 Hz, 2 H).
13C NMR (125 MHz, CDCl3): δ = 141.8, 141.1, 129.2, 128.8, 127.4, 127.2, 126.1, 126.1.
MS (EI): m/z (%) = 230 (100, [M+]), 215 (10), 202 (10), 152 (8), 115 (12).
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2′-Methyl-1,1′:3′,1′′-terphenyl (3ae)[17]
Yield: 109.8 mg (90%); white solid; mp 47–48 °C.
1H NMR (500 MHz, CDCl3): δ = 7.47–7.43 (m, 4 H), 7.42–7.35 (m, 6 H), 7.32 (dd, J = 8.6, 6.3 Hz, 1 H), 7.29–7.26 (m, 2 H), 2.15 (s, 3 H).
13C NMR (125 MHz, CDCl3): δ = 142.8, 142.4, 132.9, 129.3, 129.0, 128.1, 126.8 125.3, 18.7.
MS (EI): m/z (%) = 244 (100, [M+]), 229 (20), 215 (15), 202 (10), 165 (25), 115 (10).
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2′-Chloro-1,1′:3′,1′′-terphenyl (3af)[18]
Yield: 46.2 mg (35%); yellow solid; mp 76–77 °C.
1H NMR (500 MHz, CDCl3): δ = 7.49–7.42 (m, 8 H), 7.41–7.31 (m, 5 H).
13C NMR (125 MHz, CDCl3): δ = 141.6, 140.1, 130.4, 129.9, 129.6, 128.0, 127.5, 126.4.
MS (EI): m/z (%) = 264 (100, [M+]), 228 (30), 202 (10), 113 (20), 101 (10).
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4,4′′-Dimethyl-1,1′:3′,1′′-terphenyl (3ba)[16]
Yield: 117.4 mg (91%); white solid; mp 119–123 °C.
1H NMR (500 MHz, acetone-d 6): δ = 7.86 (s, 1 H), 7.63 (d, J = 8.1 Hz, 4 H), 7.60–7.57 (m, 2 H), 7.51 (dd, J = 8.0, 7.3 Hz, 1 H), 7.29 (d, J = 7.9 Hz, 4 H), 2.37 (s, 6 H).
13C NMR (125 MHz, acetone-d 6): δ = 142.4, 139.0, 137.9, 130.4, 130.2, 127.8, 126.3, 126.0, 21.1.
MS (EI): m/z (%) = 258 (100, [M+]), 241 (10), 228 (10), 165 (15).
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2′,4,4′′-Trimethyl-1,1′:3′,1′′-terphenyl (3be)
Yield: 121.0 mg (89%); white solid; mp 117–120 °C.
1H NMR (500 MHz, CDCl3): δ = 7.30–7.23 (m, 11 H), 2.43 (s, 6 H), 2.15 (s, 3 H).
13C NMR (125 MHz, CDCl3): δ = 142.8, 139.5, 136.4, 133.1, 129.2, 128.9, 128.7, 125.2, 21.2, 18.8.
MS (EI): m/z (%) = 272 (100, [M+]), 257 (50), 242 (20), 215 (10), 165 (15).
Anal. Calcd for C21H20: C, 92.60; H, 7.40. Found: C, 92.82; H, 7.18.
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4,4′′-Diethyl-1,1′:3′,1′′-terphenyl (3ca)
Yield: 125.8 mg (88%); white solid; mp 87 °C.
1H NMR (500 MHz, CDCl3): δ = 7.80 (s, 1 H), 7.57 (dd, J = 14.3, 7.5 Hz, 6 H), 7.52–7.46 (m, 1 H), 7.31 (d, J = 7.9 Hz, 4 H), 2.72 (q, J = 7.6 Hz, 4 H), 1.30 (t, J = 7.6 Hz, 6 H).
13C NMR (125 MHz, CDCl3): δ = 143.5, 141.7, 138.7, 129.1, 128.3, 127.2, 125.9, 125.7, 28.5, 15.5.
MS (EI): m/z (%) = 286 (90, [M+]), 271 (80), 256 (20), 2390 (13), 165 (10), 128 (35).
Anal. Calcd for C22H22: C, 92.26; H, 7.74. Found: C, 92.13; H, 7.87.
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4,4′′-Dipentyl-1,1′:3′,1′′-terphenyl (3da)
Yield: 159.1 mg (86%); white solid; mp 51 °C.
1H NMR (500 MHz, CDCl3): δ = 7.82 (s, 1 H), 7.57 (dd, J = 15.0, 4.8 Hz, 6 H), 7.50 (dd, J = 8.4, 6.8 Hz, 1 H), 7.30 (d, J = 8.0 Hz, 4 H), 2.70–2.66 (m, 4 H), 1.72–1.68 (m, 4 H), 1.41–1.37 (m, 8 H), 0.94 (t, J = 6.8 Hz, 6 H).
13C NMR (125 MHz, CDCl3): δ = 142.2, 141.7, 138.6, 129.0, 128.8, 127.1, 125.8, 125.7, 35.6, 31.6, 31.2, 22.6, 14.0.
MS (EI): m/z (%) = 370 (95, [M+]), 313 (100), 256 (30).
Anal. Calcd for C28H34: C, 90.75; H, 9.25. Found: C, 90.91; H, 9.09.
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4,4′′-Di-tert-butyl-1,1′:3′,1′′-terphenyl (3ea)[19]
Yield: 157.3 mg (92%); white solid; mp 142–146 °C.
1H NMR (500 MHz, CDCl3): δ = 7.85 (s, 1 H), 7.64 (dd, J = 8.3, 2.7 Hz, 4 H), 7.60 (dd, J = 8.2, 1.4 Hz, 2 H), 7.56–7.52 (m, 5 H), 1.69–1.20 (m, 18 H).
13C NMR (125 MHz, CDCl3): δ = 150.4, 141.6, 138.4, 129.0, 126.9, 125.9, 125.7, 34.5, 31.4.
MS (EI): m/z (%) = 342.2 (50, [M+]), 327.2 (100), 156 (20), 142 (10), 128 (25), 57.0 (40).
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4,4′′-Dimethoxy-1,1′:3′,1′′-terphenyl (3fa)[20]
Yield: 101.5 mg (70%); yellow solid; mp 184–190 °C.
1H NMR (500 MHz, CDCl3): δ = 7.72 (s, 1 H), 7.58 (d, J = 8.8 Hz, 4 H), 7.51–7.41 (m, 3 H), 7.00 (d, J = 8.8 Hz, 4 H), 3.86 (s, 6 H).
13C NMR (125 MHz, CDCl3): δ = 159.3, 141.4, 133.9, 129.1, 128.3, 125.3, 125.2, 114.3, 55.4.
MS (EI): m/z (%) = 290 (100, [M+]), 275 (30), 247 (25), 207 (14), 145 (15), 123 (8).
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3,3′′-Dimethyl-1,1′:3′,1′′-terphenyl (3ga)[21]
Yield: 110.9 mg (86%); yellow oil.
1H NMR (500 MHz, CDCl3): δ = 7.83 (d, J = 1.6 Hz, 1 H), 7.61–7.59 (m, 2 H), 7.52 (dd, J = 18.9, 8.2 Hz, 5 H), 7.39 (t, J = 7.5 Hz, 2 H), 7.23 (d, J = 7.5 Hz, 2 H), 2.48 (s, 6 H).
13C NMR (125 MHz, CDCl3): δ = 141.9, 141.3, 138.4, 129.1, 128.7, 128.2, 128.1, 126.2, 126.1, 124.4, 21.6.
MS (EI): m/z (%) = 258 (100, [M+]), 242 (10), 228 (10), 165 (15).
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4,4′′-Difluoro-1,1′:3′,1′′-terphenyl (3ha)
Yield: 86.5 mg (65%); white solid; mp 92–95 °C.
1H NMR (500 MHz, CDCl3): δ = 7.69 (s, 1 H), 7.63–7.55 (m, 4 H), 7.55–7.49 (m, 3 H), 7.15 (t, J = 8.7 Hz, 4 H).
13C NMR (125 MHz, CDCl3): δ = 163.6, 161.6, 140.9, 137.2, 129.3, 128.82, 128.75, 126.0, 125.9, 115.8, 115.6, 29.7.
MS (EI): m/z (%) = 266 (100, [M+]), 257 (50), 244 (20), 170 (5), 133 (15).
Anal. Calcd for C18H12F2: C, 81.19; H, 4.54. Found: C, 80.98; H, 4.71.
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4,4′′-Dibromo-1,1′:3′,1′′-terphenyl (3ia) and 4-Bromo-1,1′:3′,1′′-terphenyl (3ja)[22]
3ia/3ja (1.52:1); total yield: 116.4 mg (60%); white solid.
1H NMR (500 MHz, CDCl3): δ = 7.84 (s, 1 H, 3ia), 7.78 (s, 1 H, 3ja), 7.67 (dd, J = 12.5, 5.2 Hz, 4 H of 3ia and 3 H of 3ja), 7.61–7.59 (m, 4 H, 3ja), 7.55–7.51 (m, 3 H of 3ia and 1 H of 3ja), 7.49 (t, J = 7.6 Hz, 4 H of 3ia and 2 H of 3ja), 7.39 (t, J = 7.4 Hz, 2 H, 3ja).
13C NMR (125 MHz, CDCl3): δ = 142.0, 141.8, 141.2, 141.0, 140.6, 140.1, 131.9, 129.3, 129.2, 128.82, 128.78, 127.5, 127.4, 127.3, 127.2, 126.5, 126.14, 126.10, 125.89, 125.85, 121.7.
MS (EI): m/z (%), 3ia = 388 (90, [M+]), 386 (50), 389 (48), 288 (53), 113 (40).
MS (EI): m/z (%), 3ja = 308 (100, [M+]), 310 (100), 281 (25), 228 (65), 226 (45), 207 (65).
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3-(1,5-Diphenylpenta-1,4-diyn-3-yl)pentane-2,4-dione (5aa)
A reaction mixture of bispropargyl alcohol 1a (116 mg, 0.5 mmol), 1,3-diketone 2a (55 mg, 0.55 mmol), TfOH (7.5 mg, 10 mol%), and PhCl (2 mL) was placed in a 10 mL flask and stirred at 50 °C in air, monitoring the progress of the reaction periodically by TLC. Upon completion of the reaction, the solvent was removed under vacuum. The crude product was purified by flash column chromatography on silica gel (PE–EtOAc, 20:1) to afford the intermediate 5aa; yield: 149.2 mg (95%); yellow solid; mp 72.1–73 °C.
1H NMR (500 MHz, CDCl3): δ = 7.41 (dd, J = 7.5, 1.9 Hz, 4 H), 7.33–7.28 (m, 6 H), 4.65 (d, J = 10.1 Hz, 1 H), 4.23 (d, J = 10.1 Hz, 1 H), 2.35 (s, 6 H).
13C NMR (125 MHz, CDCl3): δ = 200.5, 131.7, 128.6, 128.2, 122.2, 84.0, 83.2, 72.5, 29.7, 24.2.
HRMS (ESI): m/z [M + Na]+ calcd for C22H18O2Na: 337.1204; found: 337.1199.
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Conversion of 5aa into 3aa
A reaction mixture of the intermediate 5aa (149.2 mg, 0.47 mmol) and TfOH (7.05 mg, 0.047 mmol, 10 mol%), and PhCl (2 mL) was placed in a 10 mL flask and stirred at 110 °C in air, monitoring the progress of the reaction periodically by TLC. Upon completion of the reaction, the solvent was removed under vacuum. The crude product was purified by flash column chromatography on silica gel (PE–EtOAc, 20:1) to afford the substituted benzene 3aa; yield: 99.5 mg (92%).
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Acknowledgment
We thank the Ministry of Education of China (IRT1225), National Natural Science Foundation of China (21362002 and 81260472), State Key Laboratory Cultivation Base for the Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China (CMEMR2014-A02 and CMEMR2012-A20), and Guangxi’s Medicine Talented Persons Small Highland Foundation (1306) for financial support.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org.accesdistant.sorbonne-universite.fr/10.1055/s-0035-1560372.
- Supporting Information
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For selected reviews, see:
For selected examples, see:
