ChemInform Abstract: An Efficient Radical Procedure for the Halogenation and Chalcogenation of B-Alkylcatecholboranes.

An efficient formal anti-Markovnikov addition of HX (X=Cl, Br, I, SR and SeR) to olefins under mild reaction conditions is described. The procedure is based on the hydroboration of alkenes with catecholborane. The conversion of the intermediate B-alkylcatecholboranes to the corresponding halides, sulfides and selenides is based on a common process, i.e., generation of a radical from the alkylborane followed by abstraction of a heteroatom from an aromatic sulfonyl reagent. The efficiency of these radical reactions is remarkable. The mildness of the reaction conditions is well illustrated by the preparation of iodoalkanes. Despite the notorious reactivity of iodoalkanes under radical reaction conditions, no product degradation was observed.