Organic Chemistry

Organic Photoredox Catalyzed Direct Hydroamination of Ynamides with Azoles

Authors

  • Yongming Deng Indiana University – Purdue University Indianapolis ,
  • Ban Wang Indiana University – Purdue University Indianapolis ,
  • Gavin Mccabe Indiana University – Purdue University Indianapolis ,
  • Mitchell Parrish Indiana University – Purdue University Indianapolis ,
  • Jujhar Singh Indiana University – Purdue University Indianapolis ,
  • Matthias Zeller Purdue University West Lafayette

Abstract

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.

Content

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Supplementary material

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Photoredox Catalyzed Direct Hydroamination of Ynamides with Azoles
Supplementary Materials