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N-Bromoimide/DBU Combination as a New Strategy for Intermolecular Allylic Amination

Ying Wei, Fushun Liang* and Xintong Zhang

*Department of Chemistry and Key Laboratory for UV-Emitting Materials and Technology of Ministry of Education, Northeast Normal University, Changchun 130024, China, Email: liangfs112nenu.edu.cn

Y. Wei, F. Liang, X. Zhang, Org. Lett., 2013, 15, 5186-5189.

DOI: 10.1021/ol402287n (free Supporting Information)



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Abstract

A combination of N-bromoimide and DBU enables allylic amination reactions of alkenes, in which both internal and external nitrogen nucleophiles can be installed directly. Dual activation of NBS or NBP by DBU leads to more electrophilic bromine and more nucleophilic nitrogen atoms simultaneously. This protocol provides a complementary access to allylic amination under mild conditions.

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Key Words

sulfonamides, allylic amines, NBS


ID: J54-Y2013