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Letter

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

Supporting Info

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

Process Development Division, National Chemical Laboratory, Pashan Road, Pune-411 008, India

Org. Lett., 2003, 5 (6), pp 861–864

DOI: 10.1021/ol027530f

Publication Date (Web): February 21, 2003

Corresponding author. Phone: +91-020-5893300. Fax: +91-20-5893359.

, sudalai@dalton.ncl.res.in

Abstract

A new synthetic procedure for aminohalogenation of olefins has been developed for the preparation of vicinal haloamine derivatives in high yields by using Cu, Mn, or V catalysts with p-toluenesulfonamide (TsNH₂) and N-bromosuccinimide (NBS) as nitrogen and bromine sources, respectively. Unprecedented regio- and stereoselectivity (anti:syn > 99:1) toward the aminohalogenation process is shown for olefinic substrates as well as transition metal catalysts.

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History

Published In Issue March 20, 2003
Received December 21, 2002

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Letter

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