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19.5.14.8.14 Variation 14: Cyanoselenation of Alkenes

DOI: 10.1055/sos-SD-019-00220

Murahashi, S.-I.Science of Synthesis, (200419375.

The cyanoselenation of alkenes with phenyl selenocyanate, which is readily prepared by the reaction of benzeneselenenyl chloride with trimethylsilyl cyanide, is performed in the presence of tin(IV) chloride as catalyst (Scheme 40). The addition to alkenes proceeds stereoselectively and is simple to perform. A mixture of the alkene and phenyl selenocyanate in dichloromethane is allowed to react at room temperature for 10 minutes to give the cyanoselenated compound in excellent yield.[‌185‌] Oxidation of this (phenylselanyl)nitrile with hydrogen peroxide solution over 5 minutes gives the alk-2-enenitrile.[‌185‌] By combination of these two processes, the introduction of a cyano group to the vinylic position of alkenes is readily performed.

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