Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 8, Pages 5245-5254Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b03305
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Funding
- National Natural Science Foundation of China [21778025, 21762021]
- Science and Technology Project of Jiangxi Provincial Education Department [GJJ150297, GJJ150324]
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An efficient base-promoted tandem reaction between vinyl 1,1-dichlorides and secondary sulfonamides with ynamide as the key intermediate is described. This method provides a facile approach to (Z)-1,2-endiamide and aryl 1,1-endiamide derivatives via the beta-hydroamidation of terminal ynamides and the alpha-hydroamidation of internal ynamides, respectively. This reaction proceeded through double elimination of vinyl chlorides and double addition of nucleophiles to alkynes. In addition, it features readily available starting materials, mild reaction conditions, a broad substrate scope, a wide functional group tolerance, and an operational convenience.
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