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Synthesis
DOI: 10.1055/a-2309-1501
paper

Electrochemical Oxidative Cross-Coupling for the Construction of C(sp3)–C(sp3) Bonds

Kang-Min Wen
a   Hefei National Research Center for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. of China
,
Xi-Hao Chang∗
b   School of Materials and Chemistry, Anhui Agricultural University, Hefei 230036, P. R. of China
,
Chang Guo∗
a   Hefei National Research Center for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. of China
› Author AffiliationsThis work was supported by the National Natural Science Foundation of China (grant nos. 21971227, 22222113, 22201008), the Chinese Academy of Sciences Project for Young Scientists in Basic Research (YSBR-054), the Fundamental Research Funds for the Central Universities (WK9990000090, WK9990000111), the Natural Science Foundation of Anhui Province (grant no. 2108085QB76), and the Excellent Youth Research Projects of Universities in Anhui Province (grant no. 2022AH030091).
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Abstract

A highly effective oxidation cross-coupling method involving para-cresol derivatives and malononitrile derivatives has been developed utilizing undivided electrolytic conditions. This electrochemical approach offers a robust route for synthesizing diverse malononitrile derivatives featuring quaternary carbon centers and incorporating para-phenol groups. Notably, the direct electrooxidation of the C(sp3)–H bond in the para-cresol derivative plays a crucial role in this process under electrolytic conditions. Various para-cresol derivatives and malononitrile derivatives with different substituents are readily compatible with this electrochemical transformation, affording coupling compounds in up to 99% yield.

Key words

electrochemical oxidation - cross-coupling - para-cresol derivatives - malononitrile derivatives - C(sp3)–C(sp3) bonds

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2309-1501.
  • Supporting Information


Publication History

Received: 27 February 2024

Accepted after revision: 18 April 2024

Accepted Manuscript online:
18 April 2024

Article published online:
06 May 2024

© 2024. Thieme. All rights reserved

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