Hypervalent iodine(III)-mediated oxidative decarboxylation of β,γ-unsaturated carboxylic acids

Kensuke Kiyokawa; Shunsuke Yahata; Takumi Kojima; Satoshi Minakata

doi:10.1021/ol5022433

Hypervalent iodine(III)-mediated oxidative decarboxylation of β,γ-unsaturated carboxylic acids

Org Lett. 2014 Sep 5;16(17):4646-9. doi: 10.1021/ol5022433. Epub 2014 Aug 27.

Authors

Kensuke Kiyokawa¹, Shunsuke Yahata, Takumi Kojima, Satoshi Minakata

Affiliation

¹ Department of Applied Chemistry, Graduate School of Engineering, Osaka University , Yamadaoka 2-1, Suita, Osaka 565-0871, Japan.

PMID: 25162482
DOI: 10.1021/ol5022433

Abstract

A novel oxidative decarboxylation of β,γ-unsaturated carboxylic acids mediated by hypervalent iodine(III) reagents is described. The decarboxylative C-O bond forming reaction proceeded in the presence of PhI(OAc)2 to give the corresponding allylic acetates. In addition, decarboxylative C-N bond formation was achieved by utilizing hypervalent iodine(III) reagents containing an I-N bond. Mechanistic studies suggest the unique reactivity of hypervalent iodine reagents in this ionic oxidative decarboxylation.