Tetrahedron Letters

An expedient protocol for conversion of olefins to α-bromo/iodoketones using IBX and NBS/NIS

JN Moorthy, K Senapati, N Singhal

Index: Moorthy, Jarugu Narasimha; Senapati, Kalyan; Singhal, Nidhi Tetrahedron Letters, 2009 , vol. 50, # 21 p. 2493 - 2496

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Citation Number: 45

Abstract

A variety of olefins have been shown to undergo conversion to the corresponding α- bromo/iodoketones when reacted with NBS/NIS and IBX in DMSO at room temperature. While the reaction is found to occur rapidly with e-rich arylolefins leading to the corresponding haloketones in 65–95% yields in 0.3–3.0 h, those containing e-withdrawing groups are found to yield diketones concomitantly, such that the latter are the exclusive ...