American Chemical Society
ol3c01121_si_001.pdf (4.96 MB)

Radical C(sp3)–S Coupling for the Synthesis of α‑Amino Sulfides

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journal contribution
posted on 2023-05-12, 20:33 authored by Shengzu Duan, Yujin Zi, Ya Du, Jielun Cong, Xiaotong Sun, Hong Jing, Jingfeng Zhao, Wen Chen, Xiaodong Yang
A unique transition-metal-free radical thiolation of 2-azaallyl anions has been developed. Easily accessible thiosulfonates and 2-azaallyls undergo the tandem process of single-electron transfer and radical–radical coupling to construct C­(sp3)–S bonds. This robust protocol enables a mild and chemoselective coupling between 2-azaallyl anions and thiosulfonates to access α-amino sulfides in 50–92% yields (25 examples). The scalability of this protocol was demonstrated by telescopic gram-scale experiments. Mechanistic studies provide significant evidence for this radical thiolation reaction.