Issue 24, 2018

Oxidative homodimerization of substituted olefins by DDQ visible light photocatalysis

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

Supplementary files

Article information

Article type
Research Article
Submitted
30 Jul 2018
Accepted
06 Nov 2018
First published
06 Nov 2018

Org. Chem. Front., 2018,5, 3553-3556

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, 5, 3553 DOI: 10.1039/C8QO00792F

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