硒催化的卤内酯化反应：亲电卤化试剂的亲核活化

Selenium-catalyzed halolactonization: nucleophilic activation of electrophilic halogenating reagents.

作者信息

Mellegaard Shelli R, Tunge Jon A

机构信息

Department of Chemistry, University of Kansas, Lawrence, KS 66045, USA.

出版信息

J Org Chem. 2004 Dec 10;69(25):8979-81. doi: 10.1021/jo048460o.

DOI:10.1021/jo048460o

PMID:15575789

Abstract

Diphenyl diselenide catalyzes the halolactonization of unsaturated acids with N-halosuccinimides under mild conditions. The diselenide not only accelerates the reactions, but in some cases affords regiocontrol in favor of gamma-lactone products. Experiments show that the regioselectivity in favor of gamma-lactones is a result of kinetic rather than thermodynamic control.

摘要

二苯基二硒醚在温和条件下催化不饱和酸与N-卤代琥珀酰亚胺的卤内酯化反应。该二硒醚不仅能加速反应，而且在某些情况下能实现区域选择性，有利于生成γ-内酯产物。实验表明，有利于γ-内酯生成的区域选择性是动力学控制而非热力学控制的结果。