N-heterocyclic carbenes:: deducing σ- and π-contributions in Rh-catalyzed hydroboration and Pd-catalyzed coupling reactions

被引：98

作者：

Khramov, Dimitri M. ^{[1
]}

Rosen, Evelyn L. ^{[1
]}

Er, Joyce An. ^{[1
]}

Vu, Peter D. ^{[1
]}

Lynch, Vincent M. ^{[1
]}

Bielawski, Christopher W. ^{[1
]}

机构：

[1] Univ Texas Austin, Dept Chem & Biochem, Austin, TX 78712 USA

来源：

TETRAHEDRON | 2008年 / 64卷 / 29期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/j.tet.2008.04.030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The effect of tuning the electronic properties of N-heterocyclic carbene (NHC) ligands was evaluated in multiple, mechanistically distinct, metal-mediated reactions. Hydroboration and Heck reactions, catalyzed by Rh-NHC and Pd-NHC complexes, respectively, were found to result in yields that were up to ten times lower when pi-withdrawing substituents were incorporated into the NHC backbone relative to analogues bearing sigma-withdrawing groups. (C) 2008 Elsevier Ltd. All Fights reserved.

引用

页码：6853 / 6862

页数：10

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