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: rfernand
chem.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
Details
The document discusses a study on the regioselective disulfide-catalyzed photocatalytic oxidative cleavage of 1-arylbutadienes to cinnamaldehydes. This method is highlighted for its simplicity, efficiency, and environmental friendliness, operating under mild conditions at ambient temperature with excellent regioselectivity. The process uses 2,2′-dipyridyl disulfide as a photocatalyst and oxygen as the sole oxidizing agent, activated by white LED light. The study demonstrates compatibility with a wide range of functional groups, achieving good to excellent yields across 38 examples. The method is significant due to the limited existing reports on such transformations, especially for conjugated dienes. The resulting cinnamaldehydes have numerous applications in the synthesis of natural products, bioactive molecules, and industries such as food, flavor, fragrance, and cosmetics. The study also explores the substrate scope, including various substituted 1-arylbutadienes, and provides insights into the reaction mechanism, suggesting the formation of an aryl sulfide radical. The developed method is expected to have broad applications in synthetic chemistry due to its efficiency, cost-effectiveness, and environmental benefits.
Iron(III)/O2-Mediated Regioselective Oxidative Cleavage of 1-Arylbutadienes to Cinnamaldehydes
A. Bhowmik, R. A. Fernandes, Org. Lett., 2019, 21, 9203-9207.
Key Words
cleavage of alkenes, enones, oxygen, photochemistry, organocatalysis
ID: J54-Y2022
