Selective carboxylation of reactive benzylic C-H bonds by a hypervalent iodine(III)/inorganic bromide oxidation system

An oxidation system comprising phenyliodine(III) diacetate (PIDA) and iodosobenzene with inorganic bromide, i.e., sodium bromide, in an organic solvent led to the direct introduction of carboxylic acids into benzylic C-H bonds under mild conditions. The unique radical species, generated by the homol...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2018-05, Vol.14 (1), p.1087-1094
Main Authors: Dohi, Toshifumi, Ueda, Shohei, Iwasaki, Kosuke, Tsunoda, Yusuke, Morimoto, Koji, Kita, Yasuyuki
Format: Article
Language:English
Subjects:
Acids
Carbon
Carboxylation
Carboxylic acids
Chemistry
Chromatography
C–H activation
Decomposition
Hydrocarbons
Iodine
Letter
Nitrogen
Oxidation
oxygenation
Potassium
R&D
radicals
Research & development
Sodium
Sodium bromide
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Summary:An oxidation system comprising phenyliodine(III) diacetate (PIDA) and iodosobenzene with inorganic bromide, i.e., sodium bromide, in an organic solvent led to the direct introduction of carboxylic acids into benzylic C-H bonds under mild conditions. The unique radical species, generated by the homolytic cleavage of the labile I(III)-Br bond of the in situ-formed bromo-λ -iodane, initiated benzylic carboxylation with a high degree of selectivity for the secondary benzylic position.
ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.14.94