Affiliation:
1. ICIQ—Institute of Chemical Research of Catalonia the Barcelona Institute of Science and Technology Avenida Països Catalans 16 43007 Tarragona Spain
2. University of Bologna Department of Industrial Chemistry ‘Toso Montanari' via Piero Gobetti 85 40129 Bologna Italy
Abstract
AbstractDue to their strong covalent bonds and low reduction potentials, activating inert substrates is challenging. Recent advances in photoredox catalysis offered a number of solutions, each of which useful for activating specific inert bonds. Developing a general catalytic platform that can consistently target a broad range of inert substrates would be synthetically useful. Herein, we report a readily available indole thiolate organocatalyst that, upon excitation with 405 nm light, acquires a strongly reducing power. This excited‐state reactivity served to activate, by single‐electron reduction, strong C−F, C−Cl, and C−O bonds in both aromatic and aliphatic substrates. This catalytic platform was versatile enough to promote the reduction of generally recalcitrant electron‐rich substrates (Ered<−3.0 V vs SCE), including arenes that afforded 1,4‐cyclohexadienes. The protocol was also useful for the borylation and phosphorylation of inert substrates with a high functional group tolerance. Mechanistic studies identified an excited‐state thiolate anion as responsible of the highly reducing reactivity.
Funder
Agencia Estatal de Investigación
Spanish National Plan for Scientific and Technical Research and Innovation
Cited by
3 articles.
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