Palladium-Catalyzed Heck-Type Reactions of Alkyl Iodides

被引：177

作者：

Bloome, Kayla S. ^{[1
]}

McMahen, Rebecca L. ^{[1
]}

Alexanian, Erik J. ^{[1
]}

机构：

[1] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 50期

关键词：

CROSS-COUPLING REACTIONS; CARBON-MONOXIDE; OXIDATIVE-ADDITION; BOND FORMATION; HALIDES; DERIVATIVES; COMPLEXES; CARBONYLATION; IODOALKANES; CYCLIZATION;

D O I：

10.1021/ja2091883

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A palladium-catalyzed Heck-type reaction of unactivated alkyl iodides is described. This process displays broad substrate scope with respect to both alkene and alkyl iodide components and provides efficient access to a variety of cyclic products. The reaction is proposed to proceed via a hybrid organometallic-radical mechanism, facilitating the Heck-type process with alkyl halide coupling partners. Initial intermolecular studies are also reported, demonstrating the potentially wide applicability of this approach in synthesis.

引用

页码：20146 / 20148

页数：3

共 25 条

[1] Cobalt-catalyzed trimethylsilylmethylmagnesium-promoted radical alkenylation of alkyl halides: A complement to the heck reaction [J].

Affo, Walter ;

Ohmiya, Hirohisa ;

Fujioka, Takuma ;

Ikeda, Yousuke ;

Nakamura, Tomoaki ;

Yorimitsu, Hideki ;

Oshima, Koichiro ;

Imamura, Yuki ;

Mizuta, Tsutomu ;

Miyoshi, Katsuhiko .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (24) :8068-8077

[2] Palladium-Catalyzed Carbonylative Heck-Type Reactions of Alkyl Iodides [J].

Bloome, Kayla S. ;

Alexanian, Erik J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (37) :12823-12825

[3]

Bräse S, 1998, SYNTHESIS-STUTTGART, P148

[4]

Carreira, 2011, ANGEW CHEM INT UNPUB, V50, P11125

[5] Characterization and catalytic activity of trans-[Pd(COCH2CH3) (TsO)(PPh3)2], isolated from the hydro-methoxycarbonylation of ethene catalyzed by [Pd(TsO)2(PPh3)2-] [J].

Cavinato, G ;

Toniolo, L ;

Vavasori, A .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2004, 219 (02) :233-240

[6] DISODIUM TETRACARBONYLFERRATE - TRANSITION-METAL ANALOG OF A GRIGNARD-REAGENT [J].

COLLMAN, JP .

ACCOUNTS OF CHEMICAL RESEARCH, 1975, 8 (10) :342-347

[7] Intramolecular Heck reactions of unactivated alkyl halides [J].

Firmansjah, Luke ;

Fu, Gregory C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (37) :11340-+

[8] Catalysts for cross-coupling reactions with non-activated alkyl halides [J].

Frisch, AC ;

Beller, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (05) :674-688

[9]

Hartwig J., 2009, ORGANOTRANSITION MET, P398

[10] REACTIONS OF PALLADIUM(II) COMPOUNDS WITH CARBON-MONOXIDE IN ALCOHOL-AMINE SYSTEMS - NEW ROUTE TO PALLADIUM(O) CARBONYL-PALLADIUM(II) AND CARBOALKOXY-PALLADIUM(II) COMPLEXES [J].

HIDAI, M ;

KOKURA, M ;

UCHIDA, Y .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1973, 52 (02) :431-435

← 1 2 3 →