title: Sulfinylnitriles: sulfinyl-metal exchange-alkylation strategies.
abstract: Adding organolithiums, Grignard reagents, or zincates to sulfinylnitriles triggers a facile sulfinyl-metal exchange to afford N- or C-metalated nitriles. Sulfinyl-magnesium exchange-alkylations efficiently install quaternary and tertiary centers, even in the case of tertiary sulfinylnitriles that contain a highly acidic methine proton. α-Sulfinylalkenenitriles afford moderately nucleophilic magnesiated nitriles, and the reactivity can be dramatically increased by conversion to the corresponding magnesiates. The sulfinyl-metal exchange is extremely fast, proceeds efficiently with quaternary, tertiary, and vinylic α-sulfinylnitriles, and exhibits an exceptional functional group tolerance in nitrile alkylations.
authors.affiliation: Department of Chemistry and Biochemistry, Duquesne University, 600 Forbes Ave, Pittsburgh PA 15282, USA.
authors.forename: Dinesh
authors.initials: D
authors.lastname: Nath
authors.forename: Fraser F
authors.initials: FF
authors.lastname: Fleming