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TBAI-Catalyzed Regioselective Hydroxyperoxidation of 1-Aryl/Alkyl-1,3-dienes

Atul Kumar, Gulenur N. Khatun and Rodney A. Fernandes*

*Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, Maharashtra, India, Email:

A. Kumar, G. N. Khatun, R. A. Fernandes, Org. Lett., 2023, 25, 4313-4317.

DOI: 10.1021/acs.orglett.3c01393

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TBAI catalyzes an efficient, mild, and regioselective synthesis of 4-aryl/alkyl-1-peroxy-but-3-en-2-ols in good yields from 1-substituted-1,3-butadienes in the presence of hydroperoxides and water. This regioselective orthogonal dioxygenation of a diene can be executed in a simple operation and tolerates a wide range of substrates.

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proposed mechanism

Key Words

dihydroxylation, peroxides, TBHP

ID: J54-Y2023