Photoredox Generation of Isothiouronyl Radical Cations: A New Platform in Covalent Radical Catalysis
- 28 June 2022
- journal article
- research article
- Published by Wiley in Angewandte Chemie International Edition
- Vol. 61 (32) , e202205596
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.Keywords
This publication has 43 references indexed in Scilit:
- Generation of [5.5.n] Tricyclic Ring Systems by Radical-Promoted Inter- and Intramolecular [3 + 2] CycloadditionsThe Journal of Organic Chemistry, 1997
- Versatile [3 + 2] methylenecyclopentane annulations of unactivated and electron-rich olefins with [(trimethylsilyl)methylene]cyclopropanedicarboxylatesThe Journal of Organic Chemistry, 1994
- 2,2-Dihalovinylcyclopropanes as highly diastereoselective three-atom addends in phenylthio radical mediated vinylcyclopentane synthesisJournal of the American Chemical Society, 1993
- Macrocyclization through radical-mediated vinylcyclopropane/alkene condensation. Facile entry into the brefeldin ring systemThe Journal of Organic Chemistry, 1993
- Vinylcyclopentane synthesis via phenylthio radical catalyzed alkenylation of vinylcyclopropanes: preparative and mechanistic studiesThe Journal of Organic Chemistry, 1992
- [3 + 2] Methylenecyclopentane annulations of unactivated and electron-rich olefins with 2-(phenylsulfonyl)-1-methylenecyclopropanesThe Journal of Organic Chemistry, 1990
- Formation and reactions of dithiodicarbenium saltsJournal of the American Chemical Society, 1981
- The mechanism of the electrochemical oxidation of thioureaAnalytica Chimica Acta, 1981
- Evaluation of addition rates of the thiyl radicals to vinyl monomers by flash photolysis. 2. Substituent effect on addition of substituted benzenethiyl radicals to methyl methacrylate or styreneJournal of the American Chemical Society, 1979
- Pulse radiolysis study of sulfhydryl compounds in aqueous solutionThe Journal of Physical Chemistry, 1973