Journal of the American Chemical Society

The nature of the catalytically active species in olefin dioxygenation with PhI (OAc) 2: metal or proton?

YB Kang, LH Gade

Index: Kang, Yan-Biao; Gade, Lutz H. Journal of the American Chemical Society, 2011 , vol. 133, # 10 p. 3658 - 3667

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Citation Number: 75

Abstract

Evidence for the protiocatalytic nature of the diacetoxylation of alkenes using PhI (OAc) 2 as oxidant is presented. Systematic studies into the catalytic activity in the presence of proton- trapping and metal-complexing agents indicate that protons act as catalysts in the reaction. Using triflic acid as catalyst, the selectivity and reaction rate of the conversion is similar or superior to most efficient metal-based catalysts. Metal cations, such as Pd (II) and Cu (II), ...