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CC BY 4.0 · SynOpen 2023; 07(04): 491-495
DOI: 10.1055/a-2176-1840
letter
Virtual Collection Electrochemical Organic Synthesis

Direct Electrochemical C(sp3)–H Amidation Enabled by Hexafluoroisopropanol (HFIP)

Fengyi Li‡
a   Institutes of Physical Science and Information Technology, Anhui University, Hefei, Anhui 230601, P. R. of China
,
Ke Liu‡
a   Institutes of Physical Science and Information Technology, Anhui University, Hefei, Anhui 230601, P. R. of China
,
Qi Sun
b   Hefei National Laboratory for Physical Sciences at Microscale, University of Science and Technology of China, Hefei, Anhui 230026, P. R. of China
,
Sheng Zhang∗
a   Institutes of Physical Science and Information Technology, Anhui University, Hefei, Anhui 230601, P. R. of China
,
Man-Bo Li∗
a   Institutes of Physical Science and Information Technology, Anhui University, Hefei, Anhui 230601, P. R. of China
› InstitutsangabenWe are grateful to the National Natural Science Foundation of China (21702113, 92061110, and 22001241), the Anhui University (S020318006/069 and S020118002/113), the Anhui Provincial Natural Science Foundation (2108085Y05 and 2308085Y14), and the Hefei National Laboratory for Physical Sciences at the Microscale (KF2020102) for their financial support.
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Abstract

A direct electrochemical amidation of xanthene was readily achieved under direct anodic oxidation. The reactivity of benzamides was significantly enhanced by the virtue of the solvent effect of hexafluoroisopropanol (HFIP). An obvious hydrogen bonding between HFIP and benzamide was detected, and the proton-coupled electron-transfer (PCET) effect was proposed for the enhancement effect of HFIP. In this transformation, a broad range of primary and secondary amides were readily used as amidating reagents, including l-proline-, naproxen-, and probencid-derived amides. We proposed a plausible reaction mechanism for this direct amidation based on the experimental observations.

Key words

electrochemical amidation - C(sp3)–H - hexafluoroisopropanol

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2176-1840.
  • Supporting Information


Publikationsverlauf

Eingereicht: 01. August 2023

Angenommen nach Revision: 14. September 2023

Accepted Manuscript online:
14. September 2023

Artikel online veröffentlicht:
18. Oktober 2023

© 2023. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)

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