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

下载

页码：5888 / 5890

页数：3

共 50 条

[1] Ruthenium-catalyzed Acylation of Arylpyridines with Acyl Chlorides via ortho-Selective C-H Bond Cleavage
Kochi, Takuya
Tazawa, Aoi
Honda, Kazuki
Kakiuchi, Fumitoshi
CHEMISTRY LETTERS, 2011, 40 (09) : 1018 - 1020
[2] A ruthenium-catalyzed reaction of aromatic ketones with arylboronates: A new method for the arylation of aromatic compounds via C-H bond cleavage
Kakiuchi, F. (kakiuchi@chem.eng.osaka-u.ac.jp), 1698, American Chemical Society (125):
[3] A ruthenium-catalyzed reaction of aromatic ketones with arylboronates: A new method for the arylation of aromatic compounds via C-H bond cleavage
Kakiuchi, F
Kan, S
Igi, K
Chatani, N
Murai, S
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (07) : 1698 - 1699
[4] Ruthenium-catalyzed Ortho-selective Aromatic C-H Alkenylation with Alkenyl Carbonates
Ogiwara, Yohei
Kochi, Takuya
Kakiuchi, Fumitoshi
CHEMISTRY LETTERS, 2014, 43 (05) : 667 - 669
[5] Ruthenium-Catalyzed Ortho-Selective Aromatic CH Borylation of 2-Arylpyridines with Pinacolborane
Okada, Shinsuke
Namikoshi, Takeshi
Watanabe, Shinji
Murata, Miki
CHEMCATCHEM, 2015, 7 (10) : 1531 - 1534
[6] Palladium-catalyzed ortho-selective C–H bond chlorination of aromatic ketones
Gang Shan
Gui-Yi Huang
Yu Rao
Hui Zhang
Chinese Chemical Letters, 2015, 26 (10) : 1236 - 1240
[7] Ortho-selective Arylation of Arylazoles with Aryl Bromides Catalyzed by Ruthenium Complexes
Oi, Shuichi
Sasamoto, Hiromi
Funayama, Raito
Inoue, Yoshio
CHEMISTRY LETTERS, 2008, 37 (09) : 994 - 995
[8] Palladium-catalyzed ortho-selective C-H bond chlorination of aromatic ketones
Shan, Gang
Huang, Gui-Yi
Rao, Yu
Zhang, Hui
CHINESE CHEMICAL LETTERS, 2015, 26 (10) : 1236 - 1240
[9] Ruthenium-Catalyzed Ortho-Selective C-H Alkenylation of Aromatic Compounds with Alkenyl Esters and Ethers
Ogiwara, Yohei
Tamura, Masaru
Kochi, Takuya
Matsuura, Yusuke
Chatani, Naoto
Kakiuchi, Fumitoshi
ORGANOMETALLICS, 2014, 33 (01) : 402 - 420
[10] Ruthenium-catalyzed Ortho-selective Aromatic C-H Silylation: Acceptorless Dehydrogenative Coupling of Hydrosilanes
Sakurai, Toru
Matsuoka, Yusuke
Hanataka, Tsurugi
Fukuyama, Naoaki
Namikoshi, Takeshi
Watanabe, Shinji
Murata, Miki
CHEMISTRY LETTERS, 2012, 41 (04) : 374 - 376

← 1 2 3 4 5 →