Clean and efficient benzylic C-H oxidation in water using a hypervalent iodine reagent: activation of polymeric iodosobenzene with KBr in the presence of montmorillonite-K10

Toshifumi Dohi; Naoko Takenaga; Akihiro Goto; Hiromichi Fujioka; Yasuyuki Kita

doi:10.1021/jo8012435

Clean and efficient benzylic C-H oxidation in water using a hypervalent iodine reagent: activation of polymeric iodosobenzene with KBr in the presence of montmorillonite-K10

J Org Chem. 2008 Sep 19;73(18):7365-8. doi: 10.1021/jo8012435. Epub 2008 Aug 26.

Authors

Toshifumi Dohi¹, Naoko Takenaga, Akihiro Goto, Hiromichi Fujioka, Yasuyuki Kita

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka, 565-0871 Japan.

PMID: 18729407
DOI: 10.1021/jo8012435

Abstract

We have found that unreactive and insoluble polymeric iodosobenzene [PhIO] n induced aqueous benzylic C-H oxidation to effectively give arylketones, in the presence of KBr and montmorillonite-K10 (M-K10) clay. Water-soluble and reactive species 1 having the unique I(III)-Br bond, in situ generated from [PhIO]n and KBr, was considered to be the key radical initiator during the reactions.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Bentonite / chemistry*
Bromides / chemistry*
Iodobenzenes / chemistry*
Ketones / chemical synthesis*
Ketones / chemistry
Molecular Structure
Oxidation-Reduction
Potassium Compounds / chemistry*
Stereoisomerism
Water / chemistry*

Substances

Bromides
Iodobenzenes
Ketones
Potassium Compounds
montmorillonite K-10
Water
Bentonite
potassium bromide
iodosobenzene