Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 144, Issue 20, Pages 8914-8919Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.2c03546
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Funding
- Agencia Estatal de Investigacion [PID2019-106278GB-I00, MCIN/AEI/10.13039/501100011033, CEX2019000925-S]
- China Scholarship Council for predoctoral fellowships [CSC201908310093, CSC202006920025]
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In this study, it was found that tetrachlorophthalimides can act as effective organocatalytic acceptors, triggering radical reactions not amenable to previous catalytic methods. This finding allowed the development of mechanistically distinct radical reactions and the evaluation of catalytic cycle via quantum yield measurements.
Excitation of photoactive electron donor-acceptor (EDA) complexes is an effective way to generate radicals.Applications in a catalytic regime typically use catalytic donors. Herein, we report that readily available electron-poortetrachlorophthalimides can act as effective organocatalytic acceptors to trigger the formation of EDA complexes with a variety ofradical precursors not amenable to previous catalytic methods. Excitation with visible light generates carbon radicals under mildconditions. The versatility of this EDA complex catalytic platform allowed us to develop mechanistically distinct radical reactions,including in combination with a cobalt-based catalytic system. Quantum yield measurements established that a closed catalytic cycleis operational, which hints at the ability of tetrachlorophthalimides to readily turn over and govern each catalytic cycle
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