Abstract
Phenylsulphenamides react chemoselectively with an alkene and a nitrile in the presence of trifluoromethanesulphonic acid to give N -(β-phenylthioalkyl) amidines; in the absence of nitrile an amine is formed. Regioselective 1,2-difunctionalization of alkenes with a nitrogen nucleophile and an alkylthio 1−3 or alkylseleno 1,4 group has attracted a good deal of interest recently, because it presents a simple answer to the lack of nitrogen electrophiles capable of attacking a weak nucleophile such as an alkene. 5 Reductive or oxidative elimination of the RS(e) group leads to overall addition to or substitution at the alkene by the nitrogen nucleophile (“N”) respectively (Scheme 1).
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