Visible-Light-Promoted Metal- and Photocatalyst-Free Reactions between Arylglyoxylic Acids and Tetraalkylthiuram Disulfides: Synthesis of α‑Ketoamides

A convenient and new synthetic approach has been developed for the oxidative cross-coupling of the C–N bond through the reaction between arylglyoxylic acids and tetraalkylthiuram disulfides. The reaction proceeds under ambient air at room temperature in the presence of visible light. This reaction o...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-02, Vol.89 (3), p.1473-1482
Main Authors: Sarkar, Subhankar, Pal, Satyajit, Mukherjee, Anindita, Santra, Sougata, Zyryanov, Grigory V., Majee, Adinath
Format: Article
Language:English
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Summary:A convenient and new synthetic approach has been developed for the oxidative cross-coupling of the C–N bond through the reaction between arylglyoxylic acids and tetraalkylthiuram disulfides. The reaction proceeds under ambient air at room temperature in the presence of visible light. This reaction offers a metal-, base-, photocatalyst-, and solvent-free synthesis of various α-ketoamides with moderate to excellent yields via the radical pathway. In addition, this protocol demonstrates the potential application of a gram-scale synthesis.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c02081