82795-79-7Relevant academic research and scientific papers
An efficient radical procedure for the halogenation and chalcogenation of B-alkylcatecholboranes
Schaffner, Arnaud-Pierre,Montermini, Florian,Pozzi, Davide,Darmency, Vincent,Scanlan, Eoin Martin,Renaud, Philippe
, p. 1163 - 1167 (2008)
An efficient formal anti-Markovnikov addition of HX (X = Cl, Br, I, SR and SeR) to olefins under mild reaction conditionsisdes cribed. The procedure isbas ed on the hydroboration of alkeneswith catecholborane. The conversion of the intermediate B-alkylcatecholboranesto 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 reactionsis 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 wasobs erved.
