Organic hypervalent iodine(III) catalyzed ipso-hydroxylation of aryl- and alkylboronic acids/esters

Abstract

An organo-hypervalent iodine(III) catalyzed highly efficient methodology for ipso-hydroxylation of diversely functionalized aryl- and alkylboronic acids/esters has been developed using NaIO4 as a co-oxidant. This protocol is also applicable to N-heterocyclic boronic acids and esters. Further mechanistic studies revealed that the organoboronic acid (an electron demanding moiety) is acting as a nucleophile in the presence of hypervalent iodine for hydroxylation reactions. In summary, this is the first Letter of a generalized route for organic hypervalent iodine(III) catalyzed hydroxylation of organoboronic compounds.