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

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, nam...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2020-04, Vol.22 (7), p.2288-2300
Main Authors: Mutra, Mohana Reddy, Kudale, Vishal Suresh, Li, Jing, Tsai, Wu-Hsun, Wang, Jeh-Jeng
Format: Article
Language:English
Subjects:
Alkynes
Atom economy
Crystallography
Green chemistry
Oxidants
Oxidizing agents
Substrates
Sulfur dioxide
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Summary: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–SO 2 , 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.
ISSN:1463-9262
1463-9270
DOI:10.1039/D0GC00321B