Copper-Catalyzed Diacetoxylation of Olefins using PhI(OAc)₂ as Oxidant

Jayasree Seayad*, Abdul Majeed Seayad and Christina L. L. Chai*

*Institute of Chemical and Engineering Sciences, 1 Pesek Road, Singapore 627833, Email: jayasree_seayadices.a-star.edu.sg, christina_chaiices.a-star.edu.sg

J. Seayad, A. M. Seayad, C. L. L. Chai, Org. Lett., 2010, 12, 1412-1415.

DOI: 10.1021/ol902813m

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Abstract

Copper(I) or -(II) salts with weakly coordinating anions catalyze a mild diacetoxylation of olefins efficiently in the presence of PhI(OAc)₂ as the oxidant. The reaction is effective for aryl, aryl alkyl, as well as aliphatic terminal and olefins forming the corresponding vicinal diacetoxy compounds in good yields. Internal olefins lead to syn/anti mixtures of up to 5.2.

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Key Words

dihydroxylation, iodosobenzene diacetate

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ID: J54-Y2010-0840