Catalytic Electrochemical C-H Iodination and One-Pot Arylation by ON/OFF Switching of Electric Current

被引：105

作者：

Aiso, Hiroko ^{[1
]}

Kochi, Takuya ^{[1
]}

Mutsutani, Hitoshi ^{[1
]}

Tanabe, Takamasa ^{[1
]}

Nishiyama, Shigeru ^{[1
]}

Kakiuchi, Fumitoshi ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 17期

关键词：

CROSS-COUPLING REACTIONS; AROMATIC-COMPOUNDS; BOND-CLEAVAGE; NOBEL LECTURE; PALLADIUM; HALOGENATION; OXIDATION; ARENES; ACIDS; FUNCTIONALIZATION;

D O I：

10.1021/jo3012286

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium-catalyzed electrochemical iodination and one-pot arylation of arylpyridines are described. Ortho-selective C-H iodination proceeded via dual activation of each substrate by a palladium catalyst and an electrode. Various aryl groups were introduced at the ortho positions of arylpyridines by ON/OFF switching of two different catalytic cycles using the same palladium catalyst in a one-pot fashion.

引用

页码：7718 / 7724

页数：7

共 43 条

[1] Electrochemical recycling of benzoquinone in the Pd/benzoquinone-catalyzed Heck-type reactions from arenes [J].

Amatore, Christian ;

Cammoun, Chama ;

Jutand, Anny .

ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (03) :292-296

[2] Diethyl carbonate as a solvent for ruthenium catalysed C-H bond functionalisation [J].

Arockiam, Percia ;

Poirier, Valentin ;

Fischmeister, Cedric ;

Bruneau, Christian ;

Dixneuf, Pierre H. .

GREEN CHEMISTRY, 2009, 11 (11) :1871-1875

[3] Mild C-H Halogenation of Anilides and the Isolation of an Unusual Palladium(I)-Palladium(II) Species [J].

Bedford, Robin B. ;

Haddow, Mairi F. ;

Mitchell, Charlotte J. ;

Webster, Ruth L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (24) :5524-5527

[4] Syntheses of substituted pyridines, quinolines and diazines via palladium-catalyzed cross-coupling of aryl Grignard reagents [J].

Bonnet, V ;

Mongin, F ;

Trécourt, F ;

Quéguiner, G ;

Knochel, P .

TETRAHEDRON, 2002, 58 (22) :4429-4438

[5] Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant [J].

Chen, Xiao ;

Hao, Xue-Shi ;

Goodhue, Charles E. ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6790-6791

[6] A highly selective catalytic method for the oxidative functionalization of C-H bonds [J].

Dick, AR ;

Hull, KL ;

Sanford, MS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (08) :2300-2301

[7]

Farina V., 1998, ORG REACT, V50, P1

[8] Palladium-catalyzed asymmetric iodination of unactivated C-H bonds under mild conditions [J].

Giri, R ;

Chen, X ;

Yu, JQ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (14) :2112-2115

[9] Palladium-catalyzed methylation and arylation of sp2 and sp3 C-H bonds in simple carboxylic acids [J].

Giri, Ramesh ;

Maugel, Nathan ;

Li, Jiao-Jie ;

Wang, Dong-Hui ;

Breazzano, Steven P. ;

Saunders, Lindsey B. ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (12) :3510-+

[10] High-valent organometallic copper and palladium in catalysis [J].

Hickman, Amanda J. ;

Sanford, Melanie S. .

NATURE, 2012, 484 (7393) :177-185

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