Enantioselective cyanation of propargylic C–H bonds via cooperative photoredox and copper catalysis

Yunshun Deng; Ronghua Lu; Pinhong Chen; Guosheng Liu

doi:10.1039/D3CC00410D

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Enantioselective cyanation of propargylic C–H bonds via cooperative photoredox and copper catalysis†

Yunshun Deng,‡^a Ronghua Lu,‡^b Pinhong Chen

*^b and Guosheng Liu

*^ab

Author affiliations

* Corresponding authors

^a Department of Chemistry, University of Science and Technology of China, Hefei, China
E-mail: gliu@mail.sioc.ac.cn

^b State Key Laboratory of Organometallic Chemistry, and Shanghai Hongkong Joint Laboratory in Chemical Synthesis, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, China
E-mail: pinhongchen@mail.sioc.ac.cn

Abstract

Herein, we report an enantioselective cyanation of propargylic C–H bonds by combining photoredox catalysis with a copper-catalyzed radical relay in which the propargylic radical was generated by an intramolecular 1,5-HAT process. This reaction provides easy access to optically pure propargyl nitrile compounds under mild conditions.

This article is part of the themed collection: Photofunctional Materials and Transformations

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Article information

DOI: https://doi.org/10.1039/D3CC00410D
Article type: Communication
Submitted: 29 jan. 2023
Accepted: 20 mar. 2023
First published: 21 mar. 2023
This article is Open Access

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Chem. Commun., 2023,59, 4656-4659

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Enantioselective cyanation of propargylic C–H bonds via cooperative photoredox and copper catalysis

Y. Deng, R. Lu, P. Chen and G. Liu, Chem. Commun., 2023, 59, 4656 DOI: 10.1039/D3CC00410D

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Chemical Communications

Enantioselective cyanation of propargylic C–H bonds via cooperative photoredox and copper catalysis†

Abstract

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Enantioselective cyanation of propargylic C–H bonds via cooperative photoredox and copper catalysis

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