Switchable Reactivity between Vinyl Azides and Terminal Alkyne by Nano Copper Catalysis.

Org Lett

Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering , South China University of Technology, Guangzhou 510640 , P. R. China.

Published: April 2019

A novel nano copper-catalyzed substrate-dependent chemodivergent transformation of vinyl azides with a terminal alkyne is disclosed. 2,5-Disubstituted pyrroles were selectively obtained in high yield with aryl alkynes and aliphatic alkynes, whereas 2,3,4-trisubstituted pyrroles were formed with silylated alkynes. This switchable method provides a controllable and facile access to both multisubstituted pyrrole scaffolds with high efficiency, excellent regioselectivity, and good functional group compatibility.

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http://dx.doi.org/10.1021/acs.orglett.9b00373DOI Listing

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