Organic Photoredox Catalyzed Direct Hydroamination of Ynamides with Azoles

09 December 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


Disclosed herein is a novel photoinduced selective hydroamination of ynamides with nitrogen heteroaromatic nucleophiles. By using an organocatalytic photoredox system, a direct method to construct a diverse of (Z)-α-azole enamides from ynamides and pyrazoles, as well as triazoles, benzotriazoles, indazoles, and tetrazoles, is developed, thus providing a concise route to heterocyclic motifs common in medicinal agents. Based on the mechanistic studies, the hydroamination is postulated to operate via a mechanism in which the single-electron oxidation of ynamide and the intermediacy of an alkyne radical cation, is responsible for the observed reactivity.


nitrogen heterocycles
radical cation

Supplementary materials

Photoredox Catalyzed Direct Hydroamination of Ynamides with Azoles
Supplementary Materials


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