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

ABSTRACT: 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-λ³-iodane, initiated benzylic carboxylation with a high degree of selectivity for the secondary benzylic position.

SUBMITTER: Dohi T 

PROVIDER: S-EPMC6009330 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature