Ruthenium-catalyzed arylation of fluorinated aromatic ketones via ortho-selective carbon-fluorine bond cleavage

被引：28

作者：

Kawamoto, Keisuke ^{[1
]}

Kochi, Takuya ^{[1
]}

Sato, Mitsuo ^{[1
]}

Mizushima, Eiichiro ^{[2
]}

Kakiuchi, Fumitoshi ^{[1
]}

机构：

[1] Keio Univ, Fac Sci & Technol, Dept Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan

[2] JST, PRESTO, Kawaguchi, Saitama 3320012, Japan

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 44期

关键词：

Carbon-fluorine bond cleavage; Arylation; Ruthenium catalyst; Arylboronates; Tandem arylation/alkylation; C-F BOND; OXIDATIVE ADDITION; ARYL FLUORIDES; P-C; POLYFLUOROARYL IMINES; WILKINSONS CATALYST; ANILINE DERIVATIVES; GRIGNARD-REAGENTS; COUPLING REACTION; HYDROGEN-BOND;

D O I：

10.1016/j.tetlet.2011.09.005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report here ruthenium-catalyzed arylation of fluorinated aromatic ketones via ortho-selective carbon-fluorine bond cleavage. In the presence of trimethylvinylsilane and cesium fluoride, ortho carbon-fluoride bonds of aromatic ketones were phenylated by 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane using RuH2(CO)(PPh3)(3) as a catalyst. Tandem C-F phenylation/C-H alkylation was observed for substrates bearing both one ortho hydrogen and one ortho fluorine atoms. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：5888 / 5890

页数：3

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