Photoredox Generation of Isothiouronyl Radical Cations: A New Platform in Covalent Radical Catalysis.

Angew Chem Int Ed Engl

Univ Lyon, Université Lyon 1, CNRS, INSA, CPE-Lyon, ICBMS, ICBMS, UMR 5246, Bat. Lederer, 1 rue Victor Grignard, 69622, Villeurbanne, France.

Published: August 2022

AI Article Synopsis

  • Thiyl radicals can activate alkenes covalently but face limitations in structural diversity and handling.
  • A new class of cationic sulfur-centered radicals has been developed to enhance covalent radical catalysis.
  • These radicals can be easily generated from thioureas using photoredox catalysis, showcasing their versatility in a (3+2)-radical cascade reaction.

Article Abstract

Thiyl radicals offer unique catalytic patterns for the direct covalent activation of alkenes. However, important limitations in terms of structural diversity and handling have hampered the routine use of thiyl radicals in covalent radical catalysis. Herein, we report a new class of cationic sulfur-centered radicals to achieve covalent radical catalysis. Their generation from highly modular thioureas by photoredox catalysis make their utilization very simple and reliable. The synthetic potential and the versatility of the catalytic system were finally evaluated in a (3+2)-radical cascade between vinylcyclopropanes and olefins.

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http://dx.doi.org/10.1002/anie.202205596DOI Listing

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