Regioselective Disulfide-Catalyzed Photocatalytic Oxidative Cleavage of 1-Arylbutadienes to Cinnamaldehydes

Rodney A. Fernandes*, Praveen Kumar, Amit Bhowmik and Dnyaneshwar A. Gorve

*Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, Maharashtra, India, Email: rfernandchem.iitb.ac.in

R. A. Fernandes, P. Kumar, A. Bhowmik, D. A. Gorve, Org. Lett., 2022, 24, 3436-3439.

DOI: 10.1021/acs.orglett.2c00884

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Abstract

A simple, efficient, and environmentally beneficient disulfide-catalyzed photocatalytic regioselective oxidative cleavage of 1-arylbutadienes to cinnamaldehydes offers mild reaction conditions, excellent regioselectivity, and compatibility with a wide range of functional groups.

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proposed mechanism

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Iron(III)/O₂-Mediated Regioselective Oxidative Cleavage of 1-Arylbutadienes to Cinnamaldehydes

A. Bhowmik, R. A. Fernandes, Org. Lett., 2019, 21, 9203-9207.

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Key Words

cleavage of alkenes, enones, oxygen, photochemistry, organocatalysis

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ID: J54-Y2022