[reaction: see text] 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 (TsNH(2)) 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.

N-Bromosuccinimide efficiently catalyzes the hydroamination and hydroalkoxylation of activated styrenes using tosylamides, carbamates, and alcohols as the nucleophiles to afford amino and ether derivatives, respectively. Both the processes give good to excellent yields of the products with 100% regioselectivity (Markovnikov fashion). [structure: see text]

No abstract

AminesAmines Q 0120 Transition Metal-Catalyzed Regio-and Stereoselective Aminobromination of Olefins with TsNH 2 and NBS as Nitrogen and Bromine Sources. -Cu, Mn, or V-catalyzed treatment of olefins with Tos-NH2 and NBS offers a new, regio-and stereoselective approach to vicinal aminobromides. The catalysts as well as the nature of the olefinic substituents have important effects on the regiocontrol. -(THAKUR, V. V.; TALLURI, S. K.; SUDALAI*, A.; Org. Lett. 5 (2003) 6, 861-864; Div. Process Dev., Natl. Chem. Lab., Pune 411 008, India; Eng.) -Jannicke 35-072

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