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Oxidative homodimerization of substituted olefins by DDQ visible light photocatalysis

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Abstract

A visible-light-mediated dehydrogenative homocoupling reaction of readily available mono- and disubstituted olefins to afford symmetrical di- and tetrasubstituted buta-1,3-dienes in the presence of catalytic amounts of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) has been developed. The reaction proceeds for a wide range of substrates giving buta-1,3-dienes in moderate to good yields. We propose a reaction mechanism involving direct oxidative radical coupling followed by proton and hydrogen atom elimination.

Graphical abstract: Oxidative homodimerization of substituted olefins by DDQ visible light photocatalysis

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Publication details

The article was received on 30 Jul 2018, accepted on 06 Nov 2018 and first published on 06 Nov 2018


Article type: Research Article
DOI: 10.1039/C8QO00792F
Citation: Org. Chem. Front., 2018, Advance Article
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    Oxidative homodimerization of substituted olefins by DDQ visible light photocatalysis

    D. Chuskit, R. Chaudhary, P. Venugopalan, B. König and P. Natarajan, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C8QO00792F

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