顺序烃官能团化：烯丙基C-H氧化/乙烯基C-H芳基化。

Sequential hydrocarbon functionalization: allylic C-H oxidation/vinylic C-H arylation.

作者信息

Delcamp Jared H, White M Christina

机构信息

Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA.

出版信息

J Am Chem Soc. 2006 Nov 29;128(47):15076-7. doi: 10.1021/ja066563d.

DOI:10.1021/ja066563d

PMID:17117844

Abstract

A Pd(II)/sulfoxide-catalyzed sequential allylic C-H oxidation/vinylic C-H arylation of alpha-olefins to furnish E-arylated allylic esters in high regio- and E:Z selectivities (>20:1) is reported. The broad scope of this method with respect to the alpha-olefin, carboxylic acid, and aryl boronic acid enables the rapid assembly of densely functionalized fragments for complex molecule synthesis from cheap, abundant hydrocarbon starting materials. The Pd(II)/sulfoxide-catalyzed vinylic C-H arylation of electronically unbiased olefins with aryl boronic acids proceeds under oxidative, acidic conditions and mild temperatures (room temperature to 45 degrees C).

摘要

据报道，钯（II）/亚砜催化α-烯烃的烯丙基C-H氧化/乙烯基C-H芳基化反应可高区域选择性和E:Z选择性（>20:1）地提供E-芳基化烯丙基酯。该方法对α-烯烃、羧酸和芳基硼酸具有广泛的适用性，能够从廉价、丰富的烃类起始原料快速组装用于复杂分子合成的密集官能化片段。钯（II）/亚砜催化的电子中性烯烃与芳基硼酸的乙烯基C-H芳基化反应在氧化、酸性条件和温和温度（室温至45℃）下进行。