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Hypervalent Iodine‐Induced Multi‐Component Reactions: Novel Thiocyano‐ and Isothiocyano‐phenylselenenylating Reaction of Alkenes
Author(s) -
Margarita Roberto,
Mercanti Chiara,
Parlanti Luca,
Piancatelli Giovanni
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(200005)2000:10<1865::aid-ejoc1865>3.0.co;2-i
Subject(s) - chemistry , hypervalent molecule , diphenyl diselenide , iodine , isothiocyanate , reagent , organic chemistry , alkene , medicinal chemistry , benzene , potassium thiocyanate , double bond , selenium , catalysis
A simple and efficient thiocyano‐ or isothiocyano‐phenylselenenylation of alkenes has been developed. The reactions occur when alkenes are treated with [bis(acetoxy)iodo]benzene, trimethylsilyl isothiocyanate or potassium thiocyanate and diphenyl diselenide. Mono‐ and disubstituted alkenes led to the formation of 1,2‐phenylseleno‐thiocyanates, whereas both more‐substituted alkenes and styrenes gave exclusively 1,2‐phenylseleno‐isothiocyanates. The overall transformation represents the addition of PhSeSCN to the olefinic double bonds, in situ generated by the above reagents combination.