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DOI: 10.1055/a-1379-1584
Nickel-Catalyzed Ligand-Free Hiyama Coupling of Aryl Bromides and Vinyltrimethoxysilane
This work was financially supported by the National Natural Science Foundation of China (NSF, Grant No. 91856111, 21871288, 21690074, 21821002), the Strategic Priority Research Program of the Chinese Academy of Sciences (Grant No. XDB20000000).
Abstract
We herein disclose the first Ni-catalyzed Hiyama coupling of aryl halides with vinylsilanes. This protocol uses cheap, nontoxic, and stable vinyltrimethoxysilane as the vinyl donor, proceeds under mild and ligand-free conditions, furnishing a diverse variety of styrene derivatives in high yields with excellent functional group compatibility.
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Keywords
nickel catalysis - vinylation - cross-coupling - Hiyama coupling - ligand-free conditions - vinylsilane - aryl halideStyrene derivatives represent one of the most important structural units in organic chemistry. Moreover, they serve as versatile synthetic intermediates in various organic transformations, such as olefin metathesis,[1] Heck reaction,[2] hydrofunctionalization,[3] and epoxidation.[4] Besides, they are widely used as monomers for polymer synthesis.[5] The traditional synthetic methods of styrenes include dehydration of alcohols or Hoffman elimination,[6] carbonyl olefination,[7] and semireduction of terminal alkynes.[8] However, these methods, to some extent, are limited by the accessibility of the starting materials, harsh reaction conditions, or the tolerance of functional groups.
In order to address the above-mentioned issues, numerous transition-metal-catalyzed cross-coupling reactions using readily available aryl halides have been developed to access styrenes in the past several decades.[9] For example, Pd-catalyzed vinylation of aryl halides using magnesium-,[10] lithium-,[11] aluminium-,[12] boron-,[13] silicon-,[14] and tin-based[15] vinyl donors has been reported and widely applied to the synthesis of vinyl arenes (Scheme [1a]). However, these methods generally suffer from the use of noble metal, expensive and sensitive ligand, and in some cases using toxic or unstable organometallic reagents. Therefore, a mild earth-abundant metal-catalyzed vinylation of aryl halides using stable vinyl donors is highly desirable and yet remains underdeveloped.
As the first-row transition metal in the same group as palladium, nickel has attracted much attention from the chemical community due to its earth-abundant, cost-effective characteristics, and numerous nickel-catalyzed reactions have been developed.[16] In 1972, Kumada and co-workers described a pioneering work on Ni-catalyzed cross-coupling reaction of aryl Grignard reagent with vinyl chloride (Scheme [1b]).[17] In 2009, Yamakawa and co-workers reported a Ni-catalyzed coupling of vinyl zinc reagents and aryl halides (Scheme [1c]).[18] In 2016, Gong and co-workers reported an elegant Ni-catalyzed reductive coupling of aryl halides and vinyl bromides using Zn as the reducing agent (Scheme [1d]).[19] We noted that vinylsilanes have the advantages of easy accessibility, low toxicity, and high stability, thus serve as excellent vinyl donors. Although Pd-catalyzed Hiyama coupling of aryl halides with silicon reagents is well-developed,[14] [20] the Ni-catalyzed Hiyama cross-coupling reaction is relatively underexplored.[21,22] As far as we know there is no report on the Ni-catalyzed cross-coupling reaction of vinyl silicon reagents with aryl halides. As a part of our continuous interests in nickel catalysis,[23] we herein report a ligand-free Ni-catalyzed Hiyama coupling of aryl halides with vinylsilanes to prepare styrenes (Scheme [1e]).
a Determined by GC using crude samples, the isolated yield is shown in parenthesis.
b Using 2.3 equiv of 2, KOMe, and 18-crown-6.
c Without 18-crown-6.
We started our studies by using commercially available vinyltrimethoxysilane (2) and aryl bromide 1a as model substrates and base and 18-crown-6 as activators in the presence of stable divalent nickel catalysts to optimize the reaction conditions (Table [1]). We found that inorganic bases such as KOMe, NaOMe, and KOt-Bu were effective for the vinylation reaction at ambient temperature (35 °C), affording product 3a in good yield (ca. 80%, entries 1–4), but KF led to no conversion (entry 5). The use of cyclohexane and dichloromethane as solvent resulted in low or no conversions, but more polar solvents, such as DMF, DMA, dioxane, and THF produced 3a in high yields (entries 1, 6–10). Among these solvents, DMF is the best choice. The use of different divalent nickel sources gave similar reaction outcomes (entries 11 and 12). Increasing the amount of vinylsilane and base to 2.3 equivalents could improve the yield to 87% (entry 13, 84% isolated yield). The control experiment confirmed that 18-crown-6 is critical to promote the reaction (entry 14).
Under the reaction conditions shown in Table [1], entry 13, we examined the preliminary substrate scope of this reaction. As shown in Scheme [2], we found that electronically neutral aryl bromides could furnish the corresponding vinyl arene products in 63–84% yield (3a–e). Unfortunately, an electron-rich substrate (3f) gave no conversion under ambient temperature or delivered a trace amount of product at elevated temperature (50 °C).
Interestingly, electron-deficient substrates underwent carbon–oxygen (C–O) formation to give an aryl methyl ether (3g′) but not the desired vinylation product (3g). The use of KOt-Bu as the base gave aryl methyl ether (3g′) and suggests that the methoxy group in the product results from vinyltrimethoxysilane but not from the base KOMe.[24]
To address this chemoselectivity issue, we felt the use of a more selective silane activator could be required. We noted that tetrabutylammoniumtriphenyldifluorosilicate (TBAT), a commercially available, anhydrous, nonhygroscopic, crystalline solid, was first introduced as a fluoride source by DeShong and co-workers.[25] TBAT was found less basic than tetrabutylammonium fluoride (TBAF) but could more efficiently activate silicon–carbon bonds to generate in situ carbanions to couple with electrophiles.[25] [26] Intriguingly, TBAT itself served as a phenylating agent in Pd-catalyzed cross-coupling reactions of aryl halides.[26b] However, in a Ni-catalyzed asymmetric Hiyama coupling of α-bromo esters, TBAT worked as an activator for aryltrimethoxysilane but not as a phenylating agent.[21d]
We next optimized the reaction conditions using TBAT as a nucleophilic activator for the Hiyama coupling of vinylsilane 2 and aryl bromide 1b in the presence of NiCl2(glyme) catalyst at ambient temperature (35 °C). To our delight, the new conditions afforded the vinylation product 3b in 68% yield without observing the corresponding phenylation byproduct (TBAT as a phenylating reagent) (Table [2], entry 5). Remarkably, other fluoride sources such as TBAF, KF, NaF, and CsF resulted in no conversions (entries 1–4). A solvent screening suggested DMA is the best solvent, furnishing 3b in 83% yield (entries 5–9). Other nickel sources, such as NiBr2(glyme) and NiCl2, decreased the yield slightly (entries 10 and 11). However, when increasing the amount of vinyl donor (2.0 equiv) and TBAT (2.5 equiv), the yield could be improved to 87% (83% isolated yield, entry 12). Finally, the reaction was found applicable to aryl iodide and aryl triflate affording 3b good yields, although aryl chloride and aryl tosylate were unsuitable substrates (entries 13–16).
a Determined by GC analysis. The isolated yield is shown in parenthesis.
b Using 2.0 equiv of 2 and 2.5 equiv of TBAT.
With the optimized reaction conditions in hand, we next surveyed the generality of this novel Ni-catalyzed protocol (Scheme [3]). We found that this reaction is not sensitive to steric hindrance; bulky substrates work well (3c,s). Notably, electron-deficient aryl bromides that did not work under our initial conditions (Table [1], entry 11) served as suitable substrates, affording the corresponding vinylation products in high yields (3h–u). The potential biaryl byproduct (TBAT as a phenylating reagent) and the aryl methyl ethers (methoxy migration from silane) were not observed under these mild reaction conditions. A wide variety of functional groups, including esters, aldehydes, ketones, nitriles, sulfone, amides, sulfonamides, ethers, and morpholinyl groups, were compatible (3a–y). For electron-rich aryl bromides (3w–y) and heteroaromatic substrates (3z–4e), the reactions proceeded smoothly when heating the reaction mixtures to 50 °C. Various heterocycles, such as benzothiophene, benzofuran, isoquinoline, and quinoxaline, were all competent substrates, delivering vinyl heteroarenes in good to high yields (3z–4d). However, an attempt to synthesize β-substituted styrenes using (E)-styryltriethoxysilane instead of 2 failed (4e).
Finally, we successfully performed two examples of gram-scale reactions. Similar high yields of products were obtained, which highlighting the robustness and practicality of our catalytic method (Scheme [4]).
In conclusion, we have developed a Ni-catalyzed Hiyama coupling reaction of aryl bromides and vinylsilanes for the first time.[27] The key to the success of the transformation is the use of TBAT as a silane-activating reagent. This protocol uses inexpensive nickel catalyst under ligand-free conditions, employs readily available and stable substrates, displays both high tolerance of functional groups and scale-up capacity.
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Supporting Information
- Supporting information for this article is available online at https://doi-org.accesdistant.sorbonne-universite.fr/10.1055/a-1379-1584.
- Supporting Information
-
References and Notes
- 1a Grubbs RH. Tetrahedron 2004; 60: 7117
- 1b Ogba OM, Warner NC, Grubbs RH. Chem. Soc. Rev. 2018; 47: 4510
- 2 Beletskaya IP, Cheprakov AV. Chem. Rev. 2000; 100: 3009
- 3a Chen J, Lu Z. Org. Chem. Front. 2018; 5: 260
- 3b Chen J, Guo J, Lu Z. Chin. J. Chem. 2018; 36: 1075
- 3c Fan WW, Li L, Zhang GQ. J. Org. Chem. 2019; 84: 5987
- 3d Pirnot MT, Wang Y.-M, Buchwald SL. Angew. Chem. Int. Ed. 2016; 55: 48
- 3e Agbossou F, Carpentier JF, Mortreux M. Chem. Rev. 1995; 95: 2485
- 4 Xia QH, Ge HQ, Ye CP, Liu ZM, Su KX. Chem. Rev. 2005; 105: 1603
- 5a Hirao A, Goseki R, Ishizone T. Macromolecules 2014; 47: 1883
- 5b Goseki R, Tanaka S, Ishizone T, Hirao A. React. Funct. Polym. 2018; 127: 94
- 6 Emerson WS. Chem. Rev. 1949; 45: 347
- 7a Maryanoff B, Reitz A. Chem. Rev. 1989; 89: 863
- 7b Bisceglia JA, Orelli LR. Curr. Org. Chem. 2012; 16: 2206
- 8 Chinchilla R, Najera C. Chem. Rev. 2014; 114: 1783
- 9 Denmark S, Butler CR. Chem. Commun. 2009; 20
- 10 Bumagin NA, Luzikova EV. J. Organomet. Chem. 1997; 532: 271
- 11 Hornillos V, Giannerini M, Vila C, Fañanás-Mastrala M, Feringa BL. Chem. Sci. 2015; 6: 1394
- 12 Schumann H, Kaufmann J, Schmalz H.-G, Bottcher A, Gotov B. Synlett 2003; 1783
- 13a Kerins F, O’Shea DF. J. Org. Chem. 2002; 67: 4968
- 13b Kesslers A, Coleman CM, Charoenying P, O’Shea DF. J. Org. Chem. 2004; 69: 7836
- 13c Molander GA, Rivero MR. Org. Lett. 2002; 4: 107
- 13d Barder TE, Walker SD, Martinelli JR, Buchwald SL. J. Am. Chem. Soc. 2005; 127: 4685
- 13e Alacid E, Najera C. J. Org. Chem. 2009; 74: 8191
- 13f Civicos JF, Alonso DA, Najera C. Adv. Synth. Catal. 2011; 353: 1683
- 14a Hatanaka Y, Hiyama T. J. Org. Chem. 1988; 53: 918
- 14b Itami K, Nokami T, Yoshidaj J. J. Am. Chem. Soc. 2001; 123: 5600
- 14c Hosoi K, Nozaki K, Hiyama T. Chem. Lett. 2002; 2: 138
- 14d Nakao Y, Imanaka H, Sahoo AK, Yada A, Hiyama T. J. Am. Chem. Soc. 2005; 127: 6952
- 14e Denmark SE, Sweis RF, Wehrli D. J. Am. Chem. Soc. 2004; 126: 4865
- 14f Denmark SE, Butler CR. J. Am. Chem. Soc. 2008; 130: 3690
- 14g Gordillo AL, Jesus ED, Carmen LM. J. Am. Chem. Soc. 2009; 131: 4584
- 14h Premi C, Jain N. Eur. J. Org. Chem. 2013; 5493
- 14i Yang C.-T, Han J, Liu J, Li Y, Zhang F, Yu H.-Z, Hu S, Wang X. Chem. Eur. J. 2018; 24: 10324
- 14j Faßbender SI, Molloy JJ, Mück-Lichtenfeld C, Gilmour R. Angew. Chem. Int. Ed. 2019; 58: 18619
- 15a William J, Scott WJ, Stille JK. J. Am. Chem. Soc. 1986; 108: 3033
- 15b Grasa GA, Nolan SP. Org. Lett. 2001; 3: 119
- 15c Littke AF, Schwarz L, Fu GC. J. Am. Chem. Soc. 2002; 124: 6343
- 16a Tasker SZ, Standley EA, Jamison TF. Nature 2014; 509: 299
- 16b Moragas T, Correa A, Martin R. Chem. Eur. J. 2014; 20: 8242
- 16c Cornella J, Zarate C, Martin R. Chem. Soc. Rev. 2014; 43: 8081
- 16d Su B, Cao ZC, Shi Z.-J. Acc. Chem. Res. 2015; 48: 886
- 16e Tobisu M, Chatani N. Acc. Chem. Res. 2015; 48: 1717
- 16f Weix DJ. Acc. Chem. Res. 2015; 48: 1767
- 16g Gu J, Wang X, Xue W, Gong H. Org. Chem. Front. 2015; 2: 1411
- 16h Henrion M, Ritleng V, Chetcuti MJ. ACS Catal. 2015; 5: 1283
- 16i Choi J, Fu GC. Science 2017; 356: eaaf7230
- 16j Modern Organonickel Chemistry. Tamaru Y. Wiley-VCH; Weinheim: 2006
- 17 Kiso Y, Yamamoto K, Tamao K, Kumada M. J. Am. Chem. Soc. 1972; 94: 4374
- 18 Yamamoto T, Yamakawa T. J. Org. Chem. 2009; 74: 3603
- 19 Liu J, Ren Q, Zhang X, Gong H. Angew. Chem. Int. Ed. 2016; 55: 15544
- 20a Monfared A, Mohammadi B, Ahmadi S, Nikpassan M, Hosseinian A. RSC Adv. 2019; 9: 3185
- 20b Organosilicon Chemistry. Hiyama T, Oestreich M. Wiley-VCH; Weinheim: 2019
- 20c Komiyama T, Minami Y, Hiyama T. ACS Catal. 2017; 7: 631
- 21a Lee J.-Y, Fu GC. J. Am. Chem. Soc. 2003; 125: 5616
- 21b Powell DA, Fu GC. J. Am. Chem. Soc. 2004; 126: 7788
- 21c Lee J.-Y, Fu GC. J. Am. Chem. Soc. 2003; 125: 5616
- 21d Dai X, Strotman NA, Fu GC. J. Am. Chem. Soc. 2008; 130: 3302
- 22a Tang S, Takeda M, Nakao Y, Hiyamaz T. Chem. Commun. 2011; 47: 307
- 22b Tang S, Li SH, Nakao Y, Hiyamaz T. Asian J. Org. Chem. 2013; 2: 416
- 23a Zhang W.-B, Yang X.-T, Ma J.-B, Su Z.-M, Shi S.-L. J. Am. Chem. Soc. 2019; 141: 5628
- 23b Cai Y, Zhang J.-W, Li F, Liu J.-M, Shi S.-L. ACS Catal. 2019; 9: 1
- 23c Cai Y, Ye X, Liu S, Shi S.-L. Angew. Chem. Int. Ed. 2019; 58: 13433
- 23d Shen D, Zhang W.-B, Li Z, Shi S.-L, Xu Y. Adv. Synth. Catal. 2020; 362: 1125
- 23e Li Y.-Q, Li F, Shi S.-L. Chin. J. Chem. 2020; 38: 1035
- 23f Cai Y, Ruan L.-X, Rahman A, Shi S.-L. Angew. Chem. Int. Ed. 2021; 60: in press
- 23g Li Y.-Q, Shi S.-L. Chin. J. Org. Chem. 2021; 41: in press,
- 24 For a similar Pd-catalyzed C–O bond-forming reaction using vinyltrimethoxysilane and electron-deficient aryl halides, see: Milton EJ, Fuentes JA, Clarke ML. Org. Biomol. Chem. 2009; 7: 2645
- 25a Pilcher AS, Ammon HL, DeShong P. J. Am. Chem. Soc. 1995; 117: 5166
- 25b Pilcher AS, DeShong P. J. Org. Chem. 1996; 61: 6901
- 26a Brescia M.-R, DeShong P. J. Org. Chem. 1998; 63: 3156
- 26b Mowery ME, DeShong P. J. Org. Chem. 1999; 64: 3266
- 27
General Procedure 1
In a nitrogen-filled glove box, aromatic halide (0.2 mmol, 1.0 equiv), 18-crown-6
(121.0 mg, 0.46 mmol, 2.3 equiv), KOMe (32.2 mg, 0.46 mmol, 2.3 equiv), NiCl2(glyme) (4.4 mg, 0.02 mmol, 10 mol%), and DMF (1.0 mL) were charged to an 8 mL vial
equipped with a magnetic stirrer bar. The vinyltrimethoxysilane (68.0 mg, 0.46 mmol,
2.3 equiv) was added. The vial was removed from the glove box, and the reaction mixture
was stirred at rt (35 °C) for 12 h. The reaction mixture was then diluted with EtOAc
and washed with water. The organic phase was dried over Na2SO4, filtered, and concentrated, and the residue was purified by column chromatography
on silica gel to give the product.
2-Methoxy-6-vinylnaphthalene (3a)
Using general procedure 1: white solid, 31.0 mg, yield: 84%. 1H NMR (400 MHz, CDCl3): δ = 7.78–7.66 (m, 3 H), 7.62 (dd, J = 8.7, 1.7 Hz, 1 H), 7.19–7.10 (m, 2 H), 6.87 (dd, J = 17.6, 10.9 Hz, 1 H), 5.84 (dd, J = 17.6, 0.9 Hz, 1 H), 5.30 (dd, J = 10.9, 0.9 Hz, 1 H), 3.93 (s, 3 H).
General Procedure 2
In a nitrogen-filled glove box, aromatic halide (0.2 mmol, 1.0 equiv), TBAT (270 mg,
0.5 mmol, 2.5 equiv), NiCl2(glyme) (4.4 mg, 0.02 mmol, 10 mol%), and DMA (1.0 mL) were charged to an 8 mL vial
equipped with a magnetic stirrer bar. The vinyltrimethoxysilane (59.1 mg, 0.4 mmol,
2.0 equiv) was added. The vial was removed from the glove box, and the reaction mixture
was stirred at rt (35 °C) for 12 h. The reaction mixture was then diluted with EtOAc
and washed with water. The organic phase was dried over Na2SO4, filtered, and concentrated, and the residue was purified by column chromatography
on silica gel to give the product.
2-Vinylnaphthalene (3b)
Using general procedure 2: white solid, 25.5 mg, yield: 83%. 1H NMR (400 MHz, CDCl3): δ = 7.85–7.79 (m, 3 H), 7.76 (s, 1 H), 7.65 (dd, J = 8.6, 1.7 Hz, 1 H), 7.50–7.42 (m, 2 H), 6.90 (dd, J = 17.6, 10.9 Hz, 1 H), 5.89 (dd, J = 17.6, 0.8 Hz, 1 H), 5.35 (dd, J = 10.9, 0.8 Hz, 1 H).
For selected reviews on Ni-catalyzed coupling reactions, see:
For reviews, see:
For selected examples on coupling reaction of aryl silicon compounds and alkyl halides, see:
For selected examples on coupling reaction of aryl silicon compounds and aryl halides, see:
Corresponding Authors
Publication History
Received: 30 November 2020
Accepted after revision: 31 January 2021
Accepted Manuscript online:
31 January 2021
Article published online:
16 February 2021
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
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References and Notes
- 1a Grubbs RH. Tetrahedron 2004; 60: 7117
- 1b Ogba OM, Warner NC, Grubbs RH. Chem. Soc. Rev. 2018; 47: 4510
- 2 Beletskaya IP, Cheprakov AV. Chem. Rev. 2000; 100: 3009
- 3a Chen J, Lu Z. Org. Chem. Front. 2018; 5: 260
- 3b Chen J, Guo J, Lu Z. Chin. J. Chem. 2018; 36: 1075
- 3c Fan WW, Li L, Zhang GQ. J. Org. Chem. 2019; 84: 5987
- 3d Pirnot MT, Wang Y.-M, Buchwald SL. Angew. Chem. Int. Ed. 2016; 55: 48
- 3e Agbossou F, Carpentier JF, Mortreux M. Chem. Rev. 1995; 95: 2485
- 4 Xia QH, Ge HQ, Ye CP, Liu ZM, Su KX. Chem. Rev. 2005; 105: 1603
- 5a Hirao A, Goseki R, Ishizone T. Macromolecules 2014; 47: 1883
- 5b Goseki R, Tanaka S, Ishizone T, Hirao A. React. Funct. Polym. 2018; 127: 94
- 6 Emerson WS. Chem. Rev. 1949; 45: 347
- 7a Maryanoff B, Reitz A. Chem. Rev. 1989; 89: 863
- 7b Bisceglia JA, Orelli LR. Curr. Org. Chem. 2012; 16: 2206
- 8 Chinchilla R, Najera C. Chem. Rev. 2014; 114: 1783
- 9 Denmark S, Butler CR. Chem. Commun. 2009; 20
- 10 Bumagin NA, Luzikova EV. J. Organomet. Chem. 1997; 532: 271
- 11 Hornillos V, Giannerini M, Vila C, Fañanás-Mastrala M, Feringa BL. Chem. Sci. 2015; 6: 1394
- 12 Schumann H, Kaufmann J, Schmalz H.-G, Bottcher A, Gotov B. Synlett 2003; 1783
- 13a Kerins F, O’Shea DF. J. Org. Chem. 2002; 67: 4968
- 13b Kesslers A, Coleman CM, Charoenying P, O’Shea DF. J. Org. Chem. 2004; 69: 7836
- 13c Molander GA, Rivero MR. Org. Lett. 2002; 4: 107
- 13d Barder TE, Walker SD, Martinelli JR, Buchwald SL. J. Am. Chem. Soc. 2005; 127: 4685
- 13e Alacid E, Najera C. J. Org. Chem. 2009; 74: 8191
- 13f Civicos JF, Alonso DA, Najera C. Adv. Synth. Catal. 2011; 353: 1683
- 14a Hatanaka Y, Hiyama T. J. Org. Chem. 1988; 53: 918
- 14b Itami K, Nokami T, Yoshidaj J. J. Am. Chem. Soc. 2001; 123: 5600
- 14c Hosoi K, Nozaki K, Hiyama T. Chem. Lett. 2002; 2: 138
- 14d Nakao Y, Imanaka H, Sahoo AK, Yada A, Hiyama T. J. Am. Chem. Soc. 2005; 127: 6952
- 14e Denmark SE, Sweis RF, Wehrli D. J. Am. Chem. Soc. 2004; 126: 4865
- 14f Denmark SE, Butler CR. J. Am. Chem. Soc. 2008; 130: 3690
- 14g Gordillo AL, Jesus ED, Carmen LM. J. Am. Chem. Soc. 2009; 131: 4584
- 14h Premi C, Jain N. Eur. J. Org. Chem. 2013; 5493
- 14i Yang C.-T, Han J, Liu J, Li Y, Zhang F, Yu H.-Z, Hu S, Wang X. Chem. Eur. J. 2018; 24: 10324
- 14j Faßbender SI, Molloy JJ, Mück-Lichtenfeld C, Gilmour R. Angew. Chem. Int. Ed. 2019; 58: 18619
- 15a William J, Scott WJ, Stille JK. J. Am. Chem. Soc. 1986; 108: 3033
- 15b Grasa GA, Nolan SP. Org. Lett. 2001; 3: 119
- 15c Littke AF, Schwarz L, Fu GC. J. Am. Chem. Soc. 2002; 124: 6343
- 16a Tasker SZ, Standley EA, Jamison TF. Nature 2014; 509: 299
- 16b Moragas T, Correa A, Martin R. Chem. Eur. J. 2014; 20: 8242
- 16c Cornella J, Zarate C, Martin R. Chem. Soc. Rev. 2014; 43: 8081
- 16d Su B, Cao ZC, Shi Z.-J. Acc. Chem. Res. 2015; 48: 886
- 16e Tobisu M, Chatani N. Acc. Chem. Res. 2015; 48: 1717
- 16f Weix DJ. Acc. Chem. Res. 2015; 48: 1767
- 16g Gu J, Wang X, Xue W, Gong H. Org. Chem. Front. 2015; 2: 1411
- 16h Henrion M, Ritleng V, Chetcuti MJ. ACS Catal. 2015; 5: 1283
- 16i Choi J, Fu GC. Science 2017; 356: eaaf7230
- 16j Modern Organonickel Chemistry. Tamaru Y. Wiley-VCH; Weinheim: 2006
- 17 Kiso Y, Yamamoto K, Tamao K, Kumada M. J. Am. Chem. Soc. 1972; 94: 4374
- 18 Yamamoto T, Yamakawa T. J. Org. Chem. 2009; 74: 3603
- 19 Liu J, Ren Q, Zhang X, Gong H. Angew. Chem. Int. Ed. 2016; 55: 15544
- 20a Monfared A, Mohammadi B, Ahmadi S, Nikpassan M, Hosseinian A. RSC Adv. 2019; 9: 3185
- 20b Organosilicon Chemistry. Hiyama T, Oestreich M. Wiley-VCH; Weinheim: 2019
- 20c Komiyama T, Minami Y, Hiyama T. ACS Catal. 2017; 7: 631
- 21a Lee J.-Y, Fu GC. J. Am. Chem. Soc. 2003; 125: 5616
- 21b Powell DA, Fu GC. J. Am. Chem. Soc. 2004; 126: 7788
- 21c Lee J.-Y, Fu GC. J. Am. Chem. Soc. 2003; 125: 5616
- 21d Dai X, Strotman NA, Fu GC. J. Am. Chem. Soc. 2008; 130: 3302
- 22a Tang S, Takeda M, Nakao Y, Hiyamaz T. Chem. Commun. 2011; 47: 307
- 22b Tang S, Li SH, Nakao Y, Hiyamaz T. Asian J. Org. Chem. 2013; 2: 416
- 23a Zhang W.-B, Yang X.-T, Ma J.-B, Su Z.-M, Shi S.-L. J. Am. Chem. Soc. 2019; 141: 5628
- 23b Cai Y, Zhang J.-W, Li F, Liu J.-M, Shi S.-L. ACS Catal. 2019; 9: 1
- 23c Cai Y, Ye X, Liu S, Shi S.-L. Angew. Chem. Int. Ed. 2019; 58: 13433
- 23d Shen D, Zhang W.-B, Li Z, Shi S.-L, Xu Y. Adv. Synth. Catal. 2020; 362: 1125
- 23e Li Y.-Q, Li F, Shi S.-L. Chin. J. Chem. 2020; 38: 1035
- 23f Cai Y, Ruan L.-X, Rahman A, Shi S.-L. Angew. Chem. Int. Ed. 2021; 60: in press
- 23g Li Y.-Q, Shi S.-L. Chin. J. Org. Chem. 2021; 41: in press,
- 24 For a similar Pd-catalyzed C–O bond-forming reaction using vinyltrimethoxysilane and electron-deficient aryl halides, see: Milton EJ, Fuentes JA, Clarke ML. Org. Biomol. Chem. 2009; 7: 2645
- 25a Pilcher AS, Ammon HL, DeShong P. J. Am. Chem. Soc. 1995; 117: 5166
- 25b Pilcher AS, DeShong P. J. Org. Chem. 1996; 61: 6901
- 26a Brescia M.-R, DeShong P. J. Org. Chem. 1998; 63: 3156
- 26b Mowery ME, DeShong P. J. Org. Chem. 1999; 64: 3266
- 27
General Procedure 1
In a nitrogen-filled glove box, aromatic halide (0.2 mmol, 1.0 equiv), 18-crown-6
(121.0 mg, 0.46 mmol, 2.3 equiv), KOMe (32.2 mg, 0.46 mmol, 2.3 equiv), NiCl2(glyme) (4.4 mg, 0.02 mmol, 10 mol%), and DMF (1.0 mL) were charged to an 8 mL vial
equipped with a magnetic stirrer bar. The vinyltrimethoxysilane (68.0 mg, 0.46 mmol,
2.3 equiv) was added. The vial was removed from the glove box, and the reaction mixture
was stirred at rt (35 °C) for 12 h. The reaction mixture was then diluted with EtOAc
and washed with water. The organic phase was dried over Na2SO4, filtered, and concentrated, and the residue was purified by column chromatography
on silica gel to give the product.
2-Methoxy-6-vinylnaphthalene (3a)
Using general procedure 1: white solid, 31.0 mg, yield: 84%. 1H NMR (400 MHz, CDCl3): δ = 7.78–7.66 (m, 3 H), 7.62 (dd, J = 8.7, 1.7 Hz, 1 H), 7.19–7.10 (m, 2 H), 6.87 (dd, J = 17.6, 10.9 Hz, 1 H), 5.84 (dd, J = 17.6, 0.9 Hz, 1 H), 5.30 (dd, J = 10.9, 0.9 Hz, 1 H), 3.93 (s, 3 H).
General Procedure 2
In a nitrogen-filled glove box, aromatic halide (0.2 mmol, 1.0 equiv), TBAT (270 mg,
0.5 mmol, 2.5 equiv), NiCl2(glyme) (4.4 mg, 0.02 mmol, 10 mol%), and DMA (1.0 mL) were charged to an 8 mL vial
equipped with a magnetic stirrer bar. The vinyltrimethoxysilane (59.1 mg, 0.4 mmol,
2.0 equiv) was added. The vial was removed from the glove box, and the reaction mixture
was stirred at rt (35 °C) for 12 h. The reaction mixture was then diluted with EtOAc
and washed with water. The organic phase was dried over Na2SO4, filtered, and concentrated, and the residue was purified by column chromatography
on silica gel to give the product.
2-Vinylnaphthalene (3b)
Using general procedure 2: white solid, 25.5 mg, yield: 83%. 1H NMR (400 MHz, CDCl3): δ = 7.85–7.79 (m, 3 H), 7.76 (s, 1 H), 7.65 (dd, J = 8.6, 1.7 Hz, 1 H), 7.50–7.42 (m, 2 H), 6.90 (dd, J = 17.6, 10.9 Hz, 1 H), 5.89 (dd, J = 17.6, 0.8 Hz, 1 H), 5.35 (dd, J = 10.9, 0.8 Hz, 1 H).
For selected reviews on Ni-catalyzed coupling reactions, see:
For reviews, see:
For selected examples on coupling reaction of aryl silicon compounds and alkyl halides, see:
For selected examples on coupling reaction of aryl silicon compounds and aryl halides, see:
