Tetrahedron Letters

Regio-and stereoselective hydroxybromination and dibromination of olefins using ammonium bromide and oxone®

AK Macharla, RC Nappunni, N Nama

Index: MacHarla, Arun Kumar; Chozhiyath Nappunni, Rohitha; Nama, Narender Tetrahedron Letters, 2012 , vol. 53, # 11 p. 1401 - 1405

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Citation Number: 23

Abstract

An efficient protocol for the synthesis of vicinal bromohydrins and dibromides from olefins is presented. Various olefins are regio-and stereoselectively hydroxybrominated and dibrominated with anti fashion, following Markonikov's rule, using eco-friendly, non-toxic, and stable reagents such as NH4Br and oxone® in CH3CN/H2O (1: 1) and CH3CN without employing catalyst in moderate to excellent yields. Bromohydrins are formed ...

~99%

~86%

~97%

~16%

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