Alkyltin fluorides as alkylating reagent in aminoalkylation of maleimides
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Updated: Jul 25, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Jingjing Wang1, Lin Zhao1, Yafei Zhang1
1School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou 325035, People's Republic of China. wuge@wmu.edu.cn.
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.
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