Synthesis of Complex Allylic Esters via C-H Oxidation vs C-C Bond Formation

被引：90

作者：

Vermeulen, Nicolaas A. ^{[1
]}

Delcamp, Jared H. ^{[1
]}

White, M. Christina ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 32期

关键词：

SOLID-PHASE SYNTHESIS; HYDROCARBON OXIDATION; ANTIMICROBIAL ACTIVITIES; CROSS-METATHESIS; TERMINAL ALKENES; DIRECT ARYLATION; AMINATION; FUNCTIONALIZATION; OLEFINS; ACTIVATION;

D O I：

10.1021/ja104826g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly general, predictably selective C H oxidation method for the direct, catalytic synthesis of complex allylic esters is introduced. This Pd(II)/sulfoxide-catalyzed method allows a wide range of complex aryl and alkyl carboxylic acids to couple directly with terminal olefins to furnish (E)-allylic esters in synthetically useful yields and selectivities (1 6 examples, EIZ L- 10:1) and without the use of stoichiometric coupling reagents or unstable intermediates. Strategic advantages of constructing allylic esters via C H oxidation vs C C bond-forming methods are evaluated and discussed in four "case studies".

引用

页码：11323 / 11328

页数：6

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