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An Efficient Radical Procedure for the Halogenation and Chalcogenation of B ‐Alkylcatecholboranes
Author(s) -
Schaffner ArnaudPierre,
Montermini Florian,
Pozzi Davide,
Darmency Vincent,
Scanlan Eoin Martin,
Renaud Philippe
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200700531
Subject(s) - chemistry , hydroboration , halogenation , sulfonyl , reactivity (psychology) , heteroatom , halide , markovnikov's rule , radical , reagent , radical initiator , organic chemistry , medicinal chemistry , free radical reaction , radical cyclization , regioselectivity , alkyl , catalysis , pathology , medicine , alternative medicine , polymer , polymerization
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.