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

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卷 25, 期 20, 页码 3687-3692

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c01121

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A unique transition-metal-free radical thiolation of 2-azaallylanions has been developed. This robust protocol enables the mild and chemoselective coupling between 2-azaallylanions and thiosulfonates to access alpha-amino sulfides. Mechanistic studies provide significant evidence for this radical thiolation reaction.
A unique transition-metal-free radical thiolation of2-azaallylanions has been developed. Easily accessible thiosulfonates and 2-azaallylsundergo the tandem process of single-electron transfer and radical-radicalcoupling to construct C-(sp(3))-S bonds. This robustprotocol enables a mild and chemoselective coupling between 2-azaallylanions and thiosulfonates to access alpha-amino sulfides in 50-92%yields (25 examples). The scalability of this protocol was demonstratedby telescopic gram-scale experiments. Mechanistic studies providesignificant evidence for this radical thiolation reaction.

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