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Chinese Journal of Organic Chemistry >

2024 , Vol. 44 >Issue 10: 3241 - 3248

DOI: https://doi.org/10.6023/cjoc202405025

ARTICLES

Visible-Light-Induced Selective Hydrocarboxylation of Alkynes with Formate

  • Hui Xu ,
  • Huixian Jiang ,
  • Lei Kan ,
  • Pei Xu ,
  • Xu Zhu
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  • Jiangsu Key Laboratory of New Drug Research and Clinical Pharmacy, School of Pharmacy, Xuzhou Medical University, Xuzhou, Jiangsu 221004
†These authors contributed equally to this work
*E-mail:

Received date: 2024-05-16

  Revised date: 2024-06-19

  Online published: 2024-07-25

Supported by

Jiangsu Specially-Appointed Professor Program(2020)

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Abstract

An efficient and sustainable protocol for regioselective hydrocarboxylation of alkynes to construct diverse propionic acid derivatives is disclosed. Under photoinduced conditions, the anti-Markovnikov hydrocarboxylation of alkynes was realized with CO2 radical anion in-situ generated from formate as both a carbonyl source and a reductant. The collaboration between photosensitizer and hydrogen atom transfer catalyst promoted the catalytic cycle to work smoothly, giving a broad substrate scope including terminal and internal alkynes. The Giese radical addition of CO2 radical anion to the C—C triple bond is the key step to initiate the reaction.

Key words： formate; CO2 radical anion; hydrocarboxylation; visible-light catalysis; aryl propionic acids

Cite this article

Hui Xu , Huixian Jiang , Lei Kan , Pei Xu , Xu Zhu . Visible-Light-Induced Selective Hydrocarboxylation of Alkynes with Formate[J]. Chinese Journal of Organic Chemistry, 2024 , 44(10) : 3241 -3248 . DOI: 10.6023/cjoc202405025

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