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 (free Supporting Information)
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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