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Visible-light-initiated regioselective sulfonylation/cyclization of 1,6-enynes under photocatalyst- and additive-free conditions

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Abstract

Without employing any photocatalyst and additive, an economical, eco-friendly and practical strategy has been developed for the visible-light-initiated regioselective sulfonylation/cyclization of 1,6-enynes in a biomass-derived green solvent 2-methylTHF from easily accessible sulfonyl chlorides under open-air conditions at room temperature. Compared with conventional heating conditions, the use of a 3 W blue light-emitting diode (LED) or sunlight not only reduces energy consumption but also minimizes side reactions. This transformation has excellent regioselectivity, mild reaction conditions, broad substrate scope and ease of scale-up. Moreover, mechanistic studies indicated that a sulfonyl radical pathway was involved in this reaction.

Graphical abstract: Visible-light-initiated regioselective sulfonylation/cyclization of 1,6-enynes under photocatalyst- and additive-free conditions

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Article information


Submitted
03 Nov 2019
Accepted
28 Jan 2020
First published
29 Jan 2020

Green Chem., 2020, Advance Article
Article type
Paper

Visible-light-initiated regioselective sulfonylation/cyclization of 1,6-enynes under photocatalyst- and additive-free conditions

X. Meng, Q. Kang, J. Zhang, Q. Li, W. Wei and W. He, Green Chem., 2020, Advance Article , DOI: 10.1039/C9GC03769A

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