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Hypervalent Iodine(III)-Mediated Oxidative Decarboxylation of β,γ-Unsaturated Carboxylic Acids

Kensuke Kiyokawa, Shunsuke Yahata, Takumi Kojima and Satoshi Minakata*

*Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan, Email: minakatachem.eng.osaka-u.ac.jp

K. Kiyokawa, S. Yahata, T. Kojima, S. Minakata, Org. Lett., 2014, 16, 4646-4649.

DOI: 10.1021/ol5022433 (free Supporting Information)


Abstract

An oxidative decarboxylation of β,γ-unsaturated carboxylic acids mediated by PhI(OAc)2 gives the corresponding allylic acetates. In addition, a decarboxylative C-N bond formation was achieved. Mechanistic studies suggest an unique reactivity of hypervalent iodine reagents in this ionic oxidative decarboxylation.

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Key Words

allylic alcohols, esters, allylic amines, sulfonamides, PIDA


ID: J54-Y2014