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

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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… Click to show full 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.

Keywords: photocatalyst additive; visible light; regioselective sulfonylation; initiated regioselective; sulfonylation cyclization; light initiated

Journal Title: Green Chemistry
Year Published: 2020

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