Metal-free photoinduced generation and alkynylation of carbamoyl radicals: a facile synthesis of alkynyl amides

Yurong Duan, Kai Zhang, Tongtong Xing, Yubin Bai, Jinfeng Li, Xiaojun Yang, Yu Zhao, Qiuyu Zhang

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Abstract

A metal-free photoinduced alkynylation of carbamoyl radicals with hypervalent iodine(iii) reagents for a facile synthesis of alkynyl amides is described. This protocol features good functional group tolerance and a broad substrate scope for direct synthesis of alkynyl amide derivatives in good to excellent yields under mild and redox-neutral reaction conditions. The synthetic application is demonstrated by the late-stage installation of alkynyl amides into natural products and active pharmaceutical relevant molecules. The mechanistic studies indicated the simultaneous existence of photoredox catalytic and direct photoexcited processes, and the quantum yields confirmed the occurrence of the radical chain propagation process.

Original languageEnglish
Pages (from-to)9582-9585
Number of pages4
JournalChemical Communications
Volume60
Issue number71
DOIs
StatePublished - 1 Aug 2024

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