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Alkene versus alkyne reactivity in unactivated 1,6-enynes: regio- and chemoselective radical cyclization with chalcogens under metal- and oxidant-free conditions

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Abstract

Herein, we have developed metal and oxidant-free visible light-promoted alkene vs. alkyne regio- and chemoselective radical cascade cyclization of electronically unbiased 1,6-enynes with chalcogens to synthesize substituted pyrrolidines bearing chalcogens. The reaction generated three new bonds, namely, C–SO2, C–C, and C–Se under extremely mild conditions. Furthermore, we achieved regio- and chemoselective mono-addition of aromatic thiophenols with unactivated 1,6-enynes. The key features of this protocol are broad substrate scope, environment-friendly conditions, operational simplicity, atom economy, and amenability to gram-scale synthesis. The mechanistic studies corroborate that the reaction proceeds via a radical pathway.

Graphical abstract: Alkene versus alkyne reactivity in unactivated 1,6-enynes: regio- and chemoselective radical cyclization with chalcogens under metal- and oxidant-free conditions

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Article information


Submitted
25 Jan 2020
Accepted
06 Mar 2020
First published
06 Mar 2020

Green Chem., 2020, Advance Article
Article type
Paper

Alkene versus alkyne reactivity in unactivated 1,6-enynes: regio- and chemoselective radical cyclization with chalcogens under metal- and oxidant-free conditions

M. R. Mutra, V. S. Kudale, J. Li, W. Tsai and J. Wang, Green Chem., 2020, Advance Article , DOI: 10.1039/D0GC00321B

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