Ni催化的Suzuki偶联反应
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摘要
本文主要对Ni催化的Suzuki偶联反应的发展历程和近年来碳卤键断裂类、碳氧键断裂类、碳碳键断裂类、碳氮键断裂类和碳硫键断裂类Ni催化Suzuki偶联反应进行总结。通过近十年研究,各类新型催化剂、配体、添加剂不断被开发,使反应活性大为提高,反应条件越来越温和。对目前认为Ni催化的Suzuki偶联反应的机理进行了梳理,发现Ni催化的Suzuki偶联反应催化剂循环方式有两种,即Ni(0)/Ni(Ⅱ)循环和Ni(Ⅰ)/Ni(Ⅲ)循环。因此,本文认为研究和发展价廉的金属Ni催化剂是研究Suzuki偶联反应的一个重要方向,未来Ni催化Suzuki偶联反应的研究将会集中在机理探究、新型催化剂和配体设计、多类型碳碳键构建(Csp~2-Csp~3、Csp~3-Csp~3)以及广泛底物的不对称Ni催化的Suzuki偶联反应。
Progress in Ni-catalyzed Suzuki coupling reaction including the development path and all kinds of Nicatalyzed Suzuki coupling reaction( C-Halo bond cleavage,C-O bond cleavage,C-C bond cleavage,C-N bond cleavage and C-S bond cleavage) in the past decade have been reviewed. Through nearly ten years of research,various new catalysts,ligands and additives have been developed,resulting in greatly improved reactivity and milder reaction conditions. The mechanism of Ni-catalyzed Suzuki coupling reaction was analyzed. It was found that Ni catalyzed Suzuki coupling reaction can be divided into Ni( 0)/Ni(Ⅱ) cycle and Ni(Ⅰ)/Ni(Ⅲ) cycle. It is considered that the research and development of cheap metal nickel catalyst is an important direction to study the Suzuki coupling reaction. In the future,the study of Ni catalytic Suzuki coupling reaction will focus on mechanism investigation,design of new catalysts and ligands,multi-type C-C bond construction( Csp~2-Csp~3,Csp~3-Csp~3) and asymmetric Ni-catalyzed Suzuki coupling reaction of multi-type substrates.
Progress in Ni-catalyzed Suzuki coupling reaction including the development path and all kinds of Nicatalyzed Suzuki coupling reaction( C-Halo bond cleavage,C-O bond cleavage,C-C bond cleavage,C-N bond cleavage and C-S bond cleavage) in the past decade have been reviewed. Through nearly ten years of research,various new catalysts,ligands and additives have been developed,resulting in greatly improved reactivity and milder reaction conditions. The mechanism of Ni-catalyzed Suzuki coupling reaction was analyzed. It was found that Ni catalyzed Suzuki coupling reaction can be divided into Ni( 0)/Ni(Ⅱ) cycle and Ni(Ⅰ)/Ni(Ⅲ) cycle. It is considered that the research and development of cheap metal nickel catalyst is an important direction to study the Suzuki coupling reaction. In the future,the study of Ni catalytic Suzuki coupling reaction will focus on mechanism investigation,design of new catalysts and ligands,multi-type C-C bond construction( Csp~2-Csp~3,Csp~3-Csp~3) and asymmetric Ni-catalyzed Suzuki coupling reaction of multi-type substrates.
引文
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[3]F S Han.Chem.Soc.Rev.,2013,42:5270~5298.
[4]M Irene,N Oscar.Molecules,2015,20:7528
[5]T Ryosuke,M Kei,Y Junichiro.Chem.Soc.Rev.,2017,46:5864~5888.
[6]陈国军,杜建时.有机化学,2014,34(01):65~80.
[7]V Percec,J Y Bae,D H Hill.J.Org.Chem.,1995,60:1060~1065.
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[11]A F Indolese.Tetrahed.Lett.,1997,38:3513~3516.
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[72]Q Zhou,K M Cobb,T Tan et al.J.Am.Chem.Soc.,2016,138:12057~12060.