镍催化苯酚衍生物惰性C-O键与C-H键偶联反应进展
Recent Progress in the Nickel-Catalyzed Inert C-O/C-H Cross-Coupling Reactions of Phenol Derivatives
DOI: 10.12677/AAC.2022.122010, PDF,  被引量   
作者: 曾旭群, 黄晓雷*：浙江师范大学化学与生命科学学院，浙江 金华
关键词: 镍催化；苯酚衍生物；C-O/C-H偶联；Nickel Catalysis； Phenol Derivatives； C-O/C-H Cross-Coupling
摘要: 近年来，镍催化苯酚衍生物惰性C-O键与C-H键的直接交叉偶联反应已经成为有机合成领域的研究热点。这类基于C-O/C-H偶联策略的官能化反应直接使用C-H键作为偶联底物，避免了底物的预活化，减少了有毒废物的产生，符合环境友好和步骤经济性原则。本文主要对近年来金属镍催化的苯酚衍生物惰性C-O键与烯烃、芳烃、杂环以及羰基化合物C-H键的交叉偶联反应相关研究进行了综述。
Abstract: In recent years, nickel-catalyzed inert C-O/C-H cross-coupling reactions of phenol derivatives with nucleophiles have emerged as a hot research topic in the synthetic organic chemistry community. In these reactions, C-H bonds are used as the direct coupling partners, which avoid the preactivation process, reduce the generation of wastes, and meet environmental friendly and step-economic requirements. This review summarizes the latest advancements in the nickel-catalyzed cross-coupling reactions of phenol derivatives with C-H bonds of nucleophiles such as alkenes, arenes, heterocyclic and carbonyl compounds.
文章引用：曾旭群, 黄晓雷. 镍催化苯酚衍生物惰性C-O键与C-H键偶联反应进展[J]. 分析化学进展, 2022, 12(2): 68-75. https://doi.org/10.12677/AAC.2022.122010

参考文献

[1] Han, F.S. (2013) Transition-Metal-Catalyzed Suzuki-Miyaura Cross-Coupling Reactions: A Remarkable Advance from Palladium to Nickel Catalysts. Chemical Society Reviews, 42, 5270-5298.
[Google Scholar] [CrossRef] [PubMed]
[2] Zheng, Y.L. and Newman, S.G. (2021) Cross-Coupling Reactions with Esters, Aldehydes, and Alcohols. Chemical Communications, 57, 2591-2604.
[Google Scholar] [CrossRef] 
[3] Clevenger, A.L., Stolley, R.M., Aderibigbe, A. and Louie, J. (2020) Trends in the Usage of Bidentate Phosphines as Ligands in Nickel Catalysis. Chemical Reviews, 120, 6124-6196.
[Google Scholar] [CrossRef] [PubMed]
[4] Boit, T.B., Bulger, A.S., Dander, J.E. and Garg, N.K. (2020) Activation of C-O and C-N Bonds Using Non-Precious-Metal Catalysis. ACS Catalysis, 10, 12109-12126.
[Google Scholar] [CrossRef] [PubMed]
[5] Rosen, B.M., Quasdorf, K.W., Wilson, D.A., Zhang. Na., Resmerita, A.M., Garg, N.K. and Percec, V. (2011) Nickel-Catalyzed Cross-Couplings Involving Carbon-Oxygen Bonds. Chemical Reviews, 111, 1346-1416.
[Google Scholar] [CrossRef] [PubMed]
[6] Tasker, S.Z., Standley, E.A. and Jamison, T.F. (2014) Recent Advances in Homogeneous Nickel Catalysis. Nature, 509, 299-309.
[Google Scholar] [CrossRef] [PubMed]
[7] Gensch, T., Hopkinson, M.N., Glorius, F. and Wencel-Delord, J. (2016) Mild Metal-Catalyzed C-H Activation: Examples and Concepts. Chemical Society Reviews, 45, 2900-2936.
[Google Scholar] [CrossRef] 
[8] Jeong, S. and Joo, J.M. (2021) Transition-Metal-Catalyzed Divergent C-H Functionalization of Five-Membered Heteroarenes. Accounts of Chemical Research, 54, 4518-4529.
[Google Scholar] [CrossRef] [PubMed]
[9] Walker, B.R. and Sevov, C.S. (2019) An Electrochemically Promoted, Nickel-Catalyzed Mizoroki-Heck Reaction. ACS Catalysis, 9, 7197-7203.
[Google Scholar] [CrossRef] 
[10] Ehle, A.R., Zhou, Q. and Watson, M.P. (2012) Nickel(0)-Catalyzed Heck Cross-Coupling via Activation of Aryl C-OPiv Bonds. Organic Letters, 14, 1202-1205.
[Google Scholar] [CrossRef] [PubMed]
[11] Wang, Y., Wu, S.B., Shi, W.J. and Shi, Z.J. (2016) C-O/C-H Coupling of Polyfluoroarenes with Aryl Carbamates by Cooperative Ni/Cu Catalysis. Organic Letters, 18, 2548-2551.
[Google Scholar] [CrossRef] [PubMed]
[12] Muto, K., Yamaguchi, J. and Itami, K. (2012) Nickel-Catalyzed C-H/C-O Coupling of Azoles with Phenol Derivatives. Journal of the American Chemical Society, 134, 169-172.
[Google Scholar] [CrossRef] [PubMed]
[13] Muto, K., Yamaguchi, J., Lei, A. and Itami, K. (2013) Isolation, Structure, and Reactivity of an Arylnickel(II) Pivalate Complex in Catalytic C-H/C-O Biaryl Coupling. Journal of the American Chemical Society, 135, 16384-16387.
[Google Scholar] [CrossRef] [PubMed]
[14] Xu, H.Y., Muto, K., Yamaguchi, J., Zhao, C.Y., Itami, K. and Musaev, D.G. (2014) Key Mechanistic Features of Ni-Catalyzed C-H/C-O Biaryl Coupling of Azoles and Naphthalen-2-yl Pivalates. Journal of the American Chemical Society, 136, 14834-14844.
[Google Scholar] [CrossRef] [PubMed]
[15] Lu, Q.Q., Yu, H.Z. and Fu, Y. (2014) Mechanistic Study of Chemoselectivity in Ni-Catalyzed Coupling Reactions between Azoles and Aryl Carboxylates. Journal of the American Chemical Society, 136, 8252-8260.
[Google Scholar] [CrossRef] [PubMed]
[16] Hong, X., Liang, Y. and Houk, K.N. (2014) Mechanisms and Origins of Switchable Chemoselectivity of Ni-Catalyzed C(aryl)-O and C(acyl)-O Activation of Aryl Esters with Phosphine Ligands. Journal of the American Chemical Society, 136, 2017-2025.
[Google Scholar] [CrossRef] [PubMed]
[17] Muto, K., Hatakeyama, T., Yamaguchi, J. and Itami, K. (2015) C-H Arylation and Alkenylation of Imidazoles by Nickel Catalysis: Solvent-Accelerated Imidazole C-H Activation. Chemical Science, 6, 6792-6798.
[Google Scholar] [CrossRef] 
[18] Wang, T.H., Ambre, R., Wang, Q., Lee, W.C., Wang, P.C., Liu, Y.H., Zhao, L.L. and Ong, T.J. (2018) Nickel-Catalyzed Heteroarenes Cross Coupling via Tandem C-H/C-O Activation. ACS Catalysis, 8, 11368-11376.
[Google Scholar] [CrossRef] 
[19] Takise, R., Muto, K., Yamaguchi, J. and Itami, K. (2014) Nickel-Catalyzed α-Arylation of Ketones with Phenol Derivatives. Angewandte Chemie International Edition, 53, 6791-6794.
[Google Scholar] [CrossRef] [PubMed]
[20] Koch, E., Takise, R., Studer, A., Yamaguchi, J. and Itami, K. (2015) Ni-Catalyzed α-Arylation of Esters and Amides with Phenol Derivatives. Chemical Communications, 51, 855-857.
[Google Scholar] [CrossRef] 
[21] Cornella, J., Jackson, E.P. and Martin, R. (2015) Nickel-Catalyzed Enantioselective C-C Bond Formation through Csp2-O Cleavage in Aryl Esters. Angewandte Chemie International Edition, 54, 4075-4078.
[Google Scholar] [CrossRef] [PubMed]

为你推荐