钯催化的空间位阻硼酸与α-溴代羰基化合物的交叉偶联反应。

Palladium-catalyzed cross-coupling of sterically demanding boronic acids with α-bromocarbonyl compounds.

机构信息

Department of Organic Chemistry, Technische Universität Kaiserslautern, Erwin-Schroedinger-Str. Geb. 54, 67663 Kaiserslautern, Germany.

出版信息

J Org Chem. 2011 Oct 7;76(19):8107-12. doi: 10.1021/jo2014998. Epub 2011 Sep 13.

DOI:10.1021/jo2014998

Abstract

A catalyst system generated in situ from Pd(dba)(2) and tri(o-tolyl)phosphine mediates the coupling of arylboronic acids with alkyl α-bromoacetates under formation of arylacetic acid esters at unprecedented low loadings. The new protocol, which involves potassium fluoride as the base and catalytic amounts of benzyltriethylammonium bromide as a phase transfer catalyst, is uniquely effective for the synthesis of sterically demanding arylacetic acid derivatives.

摘要

一种原位生成的钯(dba)(2)和三(邻甲苯基)膦催化剂体系介导芳基硼酸与α-溴代乙酸烷基酯的偶联反应，在前所未有的低负载下生成芳基乙酸酯。该新反应体系以氟化钾作为碱，催化量的苄基三乙基溴化铵作为相转移催化剂，对于空间位阻较大的芳基乙酸衍生物的合成具有独特的效果。

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