Merging Iridium-Catalyzed C–H Borylations with Palladium-Catalyzed Cross-Couplings using Triorganoindium Reagents

Chathurika R. K. Jayasundara, José M. Gil-Negrete, Jose R. Montero Bastidas, M. Montserrat Martínez, José Pérez Sestelo, Milton R. Smith, III, Robert E. Maleczka, Jr.


J. Org. Chem. 2022, 87, 751−759, DOI: 10.1021/acs.joc.1c01978

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A versatile and efficient method to prepare borylated arenes furnished with alkyl, alkenyl, alkynyl, aryl and heteroaryl functional groups is developed by merging Ir-catalyzed C–H borylations (CHB) with a chemoselective palladium-catalyzed cross-coupling of triorganoindium reagents (Sarandeses-Sestelo coupling) with aryl halides bearing a boronic ester substituent. Using triorganoindium cross-coupling reactions to introduce unsaturated moieties enables the synthesis of borylated arenes that would be difficult to access through the direct application of the CHB methodology. The sequential double catalyzed procedure can be also performed in one vessel.