Journal
ORGANIC LETTERS
Volume 12, Issue 24, Pages 5708-5711Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol102536s
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Funding
- Boehringer Ingelheim (Canada) Ltd.
- Natural Sciences and Engineering Research Council of Canada
- Canada Foundation for Innovation
- University of Saskatchewan
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A very efficient NHC-catalyzed lactamization reaction is reported. For most cases, the ring expansion reaction proceeds to cleanly furnish five- and six-membered N-Ts and N-Bn lactams, without the need for further purification. Evidence is presented suggesting a dual role for the stoichiometric base: (1) deprotonation of the triazolium precatalyst and (2) activation of the nitrogen leaving group through hydrogen bonding.
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