Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 21, Pages 8762-8765Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja3022818
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- [22550100]
- Grants-in-Aid for Scientific Research [22550100, 22245016] Funding Source: KAKEN
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The reaction of terminal allcynes with imines using ReBr(CO)(5) as a catalyst results in the production of N-alkylideneallylamines and not the conventional propargylamines. The substituent on the imine nitrogen is important, and a diphenylmethyl group gave the best result. The catalytic cycle of this regio selective C-C bond forming reaction appears to involve the formation of an alkynyl rhenium species and subsequent nucleophilic attack of the alkynyl beta-carbon atom on the imine carbon to give a vinylidene rhenium species.
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