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.
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.
Dohi
Toshifumi
T
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka, 565-0871 Japan.
Takenaga
Naoko
N
Goto
Akihiro
A
Fujioka
Hiromichi
H
Kita
Yasuyuki
Y
D001546:Bentonite / Q000737:chemistry*; D001965:Bromides / Q000737:chemistry*; D007462:Iodobenzenes / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D017680:Potassium Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry*
D001965:Bromides; D007462:Iodobenzenes; D007659:Ketones; D017680:Potassium Compounds; C503188:montmorillonite K-10; D014867:Water; D001546:Bentonite; C039004:potassium bromide; C037276:iodosobenzene