Alkyltin fluorides as alkylating reagent in aminoalkylation of maleimides.

ABSTRACT

Alkyltin fluoride is a frequently used electrophilic stannylation reagent via the cleavage of the Sn-F bond in traditional organic synthetic chemistry. Herein, we report the unprecedented copper-catalyzed aminoalkylation of maleimides using alkyltin fluoride as alkylating reagent through cleavage of the C-Sn bond via a radical pathway. Excellent functional group tolerance, use of O2 as green oxidant and late-stage modification of some drug intermediates are the standout features of the current toolbox. Mechanistic studies reveal that alkyltin fluorides are capable of producing alkyl radicals in a Cu/O2 catalytic system.