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One-Pot Cascade Leading to Direct α-Imidation of Ketones by a Combination of N-Bromosuccinimide and 1,8-Diazabicyclo[5.4.1]undec-7-ene

Ying Wei, Shaoxia Lin and Fushun Liang*

*Department of Chemistry, Northeast Normal University, Changchun 130024, China, Email: liangfs112nenu.edu.cn

Y. Wei, S. Lin, F. Liang, Org. Lett., 2012, 14, 4202-4205.

DOI: 10.1021/ol301871s (free Supporting Information)


Abstract

In a one-pot cascade transformation of ketones into α-imidoketones, N-bromosuccinimide (NBS) provides both electrophilic bromine and nucleophilic nitrogen sources, and diazabicyclo[5.4.1]undec-7-ene (DBU) functions as a base and a nucleophilic promoter for the activation of NBS. α-Bromination is supposed as the key step in the process.

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Key Words

imides, α-amino ketones, NBS


ID: J54-Y2012-2590