School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou 325035, People's Republic of China.
State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian 350002, China.
Org Biomol Chem. 2023 Jul 12;21(27):5643-5647. doi: 10.1039/d3ob00889d.
Alkyltin fluoride is a frequently used electrophilic stannylation reagent 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 a radical pathway. Excellent functional group tolerance, use of O 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/O catalytic system.
三氟甲磺酸烷基锡是一种常用的亲电性锡试剂，可用于传统有机合成化学中 Sn-F 键的断裂。在此，我们首次报道了三氟甲磺酸烷基锡通过 C-Sn 键断裂，以自由基途径实现马来酰亚胺的铜催化氨基烷基化反应。该方法具有良好的官能团耐受性、以 O 2 作为绿色氧化剂以及一些药物中间体的后期修饰等特点。反应机理研究表明，三氟甲磺酸烷基锡在 Cu/O 催化体系中能够生成烷基自由基。
