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1,3-卤原子迁移作为一种从不常见起始原料制备芳基铜的方法。

1,3-Halogen migration as an entry to aryl coppers from an unintuitive starting material.

作者信息

Van Hoveln R J, Schmid S C, Schomaker J M

机构信息

Department of Chemistry, University of Wisconsin, 1101 University Ave., Madison, Wisconsin 53706, USA.

出版信息

Org Biomol Chem. 2014 Oct 21;12(39):7655-8. doi: 10.1039/c4ob01294a. Epub 2014 Aug 19.

Abstract

A copper(I) catalyzed 1,3-halogen migration/borylation migrates a bromine from an sp(2) carbon to a benzylic carbon with concomitant borylation of the aryl-bromine bond. This transformation proceeds via an aryl copper intermediate which can be accessed independently and then trapped with electrophiles. As such, copper-catalyzed 1,3-halogen migration provides unique and mild access to an aryl copper species that allows for rapid aromatic functionalization from an unconventional starting material.

摘要

铜(I)催化的1,3-卤原子迁移/硼化反应可将溴从sp(2) 碳迁移至苄基碳,同时实现芳基 - 溴键的硼化。该转化过程经由芳基铜中间体进行,该中间体可独立生成,随后与亲电试剂捕获。因此,铜催化的1,3-卤原子迁移为生成芳基铜物种提供了独特且温和的途径,使得能够从非常规起始原料快速实现芳烃官能化。

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