Synthesis of nitrogen-tethered 1,6-enynes through CuI/TFA catalysis
Literature Information
Publication Date
2021-12-03
DOI
10.1039/D1QO01358K
Impact Factor
5.281
Authors
Leilei Cao, Liliang Huang, Xianjun Xu
View Original
Abstract
A novel method for the concise and effective construction of nitrogen-tethered 1,6-enynes in moderate to good yields was developed. This transformation involves a TFA-promoted Pictet–Spengler reaction/iminium formation, copper-catalyzed alkyne–iminium ene reaction/alkynylation of a 2-arylethan-1-amine, formaldehyde solution, and a terminal alkyne. The process features exclusive chemoselectivity, simple operation, and high atom economy. Preliminary experimental studies suggest that the alkyne–iminium ene reaction involving an intermolecular hydride transfer is the key step in the current methodology.
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Source Journal
Organic Chemistry Frontiers
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7.8
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