Transition Metal-Catalyzed Regio- and Stereoselective Aminobromination of Olefins with TsNH₂ and NBS as Nitrogen and Bromine Sources

Vinay V. Thakur, Siva Kumar Talluri and A. Sudalai*

*Process Development Division, National Chemical Laboratory, Pashan Road, Pune-411 008, India, Email: a.sudalaincl.res.in

V. V. Thakur, S. K. Talluri, A. Sudalai, Org. Lett., 2003, 5, 861-864.

DOI: 10.1021/ol027530f

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Abstract

A new procedure for aminobromination of olefins gives vicinal bromoamine derivatives in high yields using Cu, Mn, or V catalysts with p-toluenesulfonamide as nitrogen source and N-bromosuccinimide (NBS) as bromine source. Excellent regio- and stereoselectivity is shown for different olefinic substrates as well as transition metal catalysts.

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Key Words

Aminobromination, Sulfonamides, N-Bromosuccinimide, Bromination

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ID: J54-Y2003-340