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. 2012 Aug 17;14(16):4202-5.
doi: 10.1021/ol301871s. Epub 2012 Aug 3.

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

Affiliations

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 et al. Org Lett. .

Abstract

A one-pot cascade transformation of ketones into α-imidoketones has been developed, in which 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, which takes place between more electrophilic bromide active species and enolates.

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