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

Narasimha Moorthy, Jarugu ; Senapati, Kalyan ; Singhal, Nidhi (2009) An expedient protocol for conversion of olefins to α-bromo/iodoketones using IBX and NBS/NIS Tetrahedron Letters, 50 (21). pp. 2493-2496. ISSN 0040-4039

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/j.tetlet.2009.03.032

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 products over extended duration of the reactions.

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