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Updated: Jun 26, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Sterically Diversified C(sp3)-C(sp3) Coupling between Ketone and Carboxylic Acid-Derived Radical Precursors via
Jian-Xiong Yang1,2, Jia-Run Wang1, Chang Liu3
1Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai Frontiers Science Center of Drug Target Identification and Delivery, National Key Laboratory of Innovative Immunotherapy, School of Pharmaceutical Sciences, Shanghai Jiao Tong University, Shanghai 200240, P. R. China.
Abstract:
We report a synergistic photoredox and nickel-catalyzed strategy for sterically diversified fragment coupling between preactivated ketones and carboxylic acids. By employing prearomatic intermediates and redox-active esters, distinct alkyl radicals generated via a photoredox-neutral process undergo nickel-catalyzed SH2 homolytic substitution to achieve heteroselective radical-radical coupling. This synthetic platform features optimal steric diversification, as both ketones and acids can orthogonally serve as primary, secondary, and tertiary radical precursors, enabling facile access to construct diverse C(sp3)-C(sp3) linkages, including the particularly challenging all-carbon quaternary centers.
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