Chelation-Assisted Regioselective Catalytic Functionalization of C-H, C-O, C-N and C-F Bonds

被引:87
|
作者
Kakiuchi, Fumitoshi [1 ,2 ]
Kochi, Takuya [1 ]
Murai, Shinji [3 ,4 ]
机构
[1] Keio Univ, Fac Sci & Technol, Dept Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan
[2] JST, ACT C, Kawaguchi, Saitama 3320012, Japan
[3] Nara Inst Sci & Technol, Ikoma, Nara 6300192, Japan
[4] Osaka Univ, Suita, Osaka 565, Japan
关键词
alkylation; arylation; alkenylation; introduction of carbonyl groups; halogenation; polycyclic aromatic hydrocarbons; CARBON-HYDROGEN BONDS; CROSS-COUPLING REACTION; DIRECT ORTHO ARYLATION; PROTON-ABSTRACTION MECHANISM; DIRECT ORTHO-ALKENYLATION; AROMATIC KETONES; OXIDATIVE ADDITION; ANILINE DERIVATIVES; GRIGNARD-REAGENTS; RUTHENIUM COMPLEX;
D O I
10.1055/s-0034-1379210
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Transition-metal-catalyzed functionalization of unreactive carbon bonds such as C-H, C-O, C-N, and C-F bonds has been extensively studied over the last two decades. In this account we describe our studies on chelation-assisted catalytic transformations of unreactive carbon bonds in aromatic and olefinic compounds. Various C-C bond forming reactions are achieved by catalytic addition of C-H bonds to alkenes and alkynes, and via coupling reactions such as those of C-H, C-O, C-N, and C-F bonds with boronic esters. Methods for the conversion of C-H bonds into C-Si and C-X (X = halogen) bonds are also developed. The C-C bond forming reactions are applied to short syntheses of polycyclic aromatic hydrocarbons.
引用
收藏
页码:2390 / 2414
页数:25
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