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Umpolung Reactivity of Fluoroalkylselenotoluenesulfonates: Towards a Versatile Reagent
Author(s) -
Ghiazza Clément,
Kataria Alex,
Tlili Anis,
Toulgoat Fabien,
Billard Thierry
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900027
Subject(s) - chemistry , umpolung , reagent , electrophile , nucleophile , trifluoromethyl , reactivity (psychology) , halide , alkyl , ethylene , medicinal chemistry , nucleophilic substitution , organic chemistry , combinatorial chemistry , catalysis , medicine , alternative medicine , pathology
Fluoroalkylselenotoluenesulfonates, which have already been described as selenolating reagents in electrophilic and radical reactions, can also be reduced by an organic electron donor (namely tetrakis(dimethylamino) ethylene or TDAE) to generate the corresponding fluoroalkylselenolate anions. Thus, the in‐situ‐formed anions react with various alkyl halides in a metal‐free nucleophilic substitution. Trifluoromethyl‐ and higher perfluroalkylselenolated compounds have been obtained in modest to good yields.