Carbon-Based Leaving Group in Substitution Reactions: Functionalization of sp3-Hybridized Quaternary and Tertiary Benzylic Carbon Centers

被引：34

作者：

Mahoney, Stuart J. ^{[1
]}

Lou, Tiantong ^{[1
]}

Bondarenko, Ganna ^{[1
]}

Fillion, Eric ^{[1
]}

机构：

[1] Univ Waterloo, Dept Chem, Waterloo, ON N2L 3G1, Canada

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 13期

基金：

加拿大自然科学与工程研究理事会;

关键词：

C-C BOND; ACTIVATION; CLEAVAGE; DEALLYLATION;

D O I：

10.1021/ol301442z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lewis acid promoted substitution reactions employing Meldrum's acid and 5-methyl Meldrum's acid as carbon-based leaving groups are described which transform unstrained quaternary and tertiary benzylic C-sp3-C-sp3 bonds into C-sp3-X bonds (X = C, H, N). Importantly, this reaction has a broad scope in terms of both suitable substrates and nucleophiles with good to excellent yields obtained (typically >90%).

引用

页码：3474 / 3477

页数：4