Organic Letters 2013-10-18

N-bromoimide/DBU combination as a new strategy for intermolecular allylic amination.

Ying Wei, Fushun Liang, Xintong Zhang

Index: Org. Lett. 15(20) , 5186-9, (2013)

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Abstract

Allylic amination reactions of alkenes, with an NBP (N-bromophthalimide) or NBS (N-bromosuccinimide)/DBU combination, were developed, 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 may provide a novel and complementary access to allylic amination under mild conditions.