Oxygen and base-free oxidative heck reactions of arylboronic acids with olefins

被引：165

作者：

Ruan, Jiwu ^{[1
]}

Li, Xinming ^{[1
]}

Saidi, Ourida ^{[1
]}

Xiao, Jianliang ^{[1
]}

机构：

[1] Univ Liverpool, Dept Chem, Liverpool Ctr Mat & Catalysis, Liverpool L69 7ZD, Merseyside, England

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 08期

关键词：

D O I：

10.1021/ja0782955

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A mild and efficient protocol for palladium-catalyzed oxidative Heck reactions of arylboronic acids with both electron-rich and -deficient olefins is described. In contrast to the normal oxidative Heck coupling, this new method works in the absence of a base, oxygen, or other external oxidants. With a wide variety of substrates tolerated, the method broadens the scope of palladium-catalyzed coupling reactions.

引用

收藏

页码：2424 / 2425

页数：2

相关论文

共 28 条

[1] Mechanism of the palladium-catalyzed homocoupling of arylboronic acids: Key involvement of a palladium peroxo complex [J].

Adamo, Carlo ;

Amatore, Christian ;

Ciofini, Ilaria ;

Jutand, Anny ;

Lakmini, Hakim .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6829-6836

[2] Enantioselective Heck-type reaction catalyzed by tropos-Pd(II) complex with chiraphos ligand [J].

Akiyama, K ;

Wakabayashi, K ;

Mikami, K .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) :1569-1575

[3] Non-conventional methodologies for transition-metal catalysed carbon-carbon coupling: a critical overview. Part 1: The Heck reaction [J].

Alonso, F ;

Beletskaya, IP ;

Yus, M .

TETRAHEDRON, 2005, 61 (50) :11771-11835

[4] Dioxygen-promoted regioselective oxidative Heck arylations of electron-rich olefins with arylboronic acids [J].

Andappan, MMS ;

Nilsson, P ;

von Schenck, H ;

Larhed, M .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (16) :5212-5218

[5] The first ligand-modulated oxidative Heck vinylation. Efficient catalysis with molecular oxygen as palladium(0) oxidant [J].

Andappan, MMS ;

Nilsson, P ;

Larhed, M .

CHEMICAL COMMUNICATIONS, 2004, (02) :218-219

[6] Arylboronic acids as versatile coupling partners in fast microwave promoted oxidative Heck chemistry [J].

Andappan, Murugaiah M. S. ;

Nilsson, Peter ;

Larhed, Mats .

MOLECULAR DIVERSITY, 2003, 7 (2-4) :97-106

[7] The heck reaction as a sharpening stone of palladium catalysis [J].

Beletskaya, IP ;

Cheprakov, AV .

CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066

[8]

BLATTER K, 1989, SYNTHESIS-STUTTGART, P356

[9] PALLADIUM-CATALYZED CROSS-COUPLING OF ARYL AND ALKENYL BORONIC ACIDS WITH ALKENES VIA OXIDATIVE ADDITION OF A CARBON-BORON BOND TO PALLADIUM(0) [J].

CHO, CS ;

UEMURA, S .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 465 (1-2) :85-92

[10] [2]Rotaxanes through palladium active-template oxidative Heck cross-couplings [J].

Crowley, James D. ;

Hanni, Kevin D. ;

Lee, Ai-Lan ;

Leigh, David A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (40) :12092-+