Journal
ORGANIC LETTERS
Volume 14, Issue 17, Pages 4662-4665Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol302102h
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Funding
- NSF [CAREER CHE-0969157]
- UCSB
- China Science Council
- East China Normal University
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0969157] Funding Source: National Science Foundation
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The cyclic alpha-imino gold carbene intermediate B is most likely generated in situ via regioselective nitrene transfer from an azido group to a tethered terminal alkyne in the presence of a gold catalyst and at ambient temperature. This highly electrophilic intermediate can react with a weakly nucleophilic nitrile, which is used as the reaction solvent, to deliver a bicyclic imidazole rapidly in an overall bimolecular [2 + 2 + 1] cycloaddition and in mostly serviceable yield. The competing intramolecular Huisgen reaction, although likely also catalyzed by gold, is minimized by using AuCl3 as the catalyst.
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