Palladium-Catalyzed Allylic Cross-Coupling Reactions of Primary and Secondary Homoallylic Electrophiles

被引：78

作者：

Stokes, Benjamin J. ^{[1
]}

Opra, Susanne M. ^{[1
]}

Sigman, Matthew S. ^{[1
]}

机构：

[1] Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 28期

基金：

美国国家卫生研究院;

关键词：

C-H ALKYLATION; OXIDATIVE ADDITION; ORGANOMETALLIC COMPOUNDS; SP(3) CARBON; DOUBLE-BOND; HALIDES; LIGANDS; ACTIVATION; MECHANISM; ALKENES;

D O I：

10.1021/ja305403s

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The Pd(0)-catalyzed allylic cross-coupling of homoallylic tosylate substrates using boronic acids and pinacol esters is reported. The reaction uses 2-(4,5-dihydro-2-oxazolyl)quinoline (quinox) as a ligand and is performed at ambient temperature. The scope of the reaction is broad in terms of both the boronate transmetalating reagent and the substrate and includes secondary tosylates. Mechanistic studies support an alkene-mediated S(N)2-type stereoinvertive oxidative addition of unactivated primary and secondary alkyl tosylates.

引用

页码：11408 / 11411

页数：4

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