Journal
CHEMICAL COMMUNICATIONS
Volume 55, Issue 76, Pages 11478-11481Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9cc05385a
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Funding
- Natural Science Foundation of the Jiangsu Higher Education Institutions of China [18KJA350001]
- Priority Academic Program Development of the Jiangsu Higher Education Institutes (PAPD)
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A regioselective cis-hydroalkylation of internal alkynes with readily prepared Katritzky pyridinium salts for the synthesis of tri-substituted alkenes is described. This reaction is the first example of a metal-catalyzed hydroalkylation of an alkyne via C-N bond activation of an amine. The reaction demonstrates broad scope and functional group tolerance, allowing access to desired products with high diversity. Preliminary mechanistic studies indicate that a combination of an SET-initiated radical process and Ni-catalyzed alkylation could engage in the reaction, which makes it possible to bypass the traditional open-shell addition pathway.
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