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Bismuth-Catalyzed Photoinduced Ligand-to-Metal Charge Transfer (LMCT) Hydrodecarbonylation of Aldehydes
Lucas F Villela1, Timothée Stoerkler1, Liam Labbé1
1Department of Chemistry and Biomolecular Science, University of Ottawa, Ottawa, Ontario K1N 6N5, Canada.
Abstract:
Herein, we disclose a visible-light, bismuth-catalyzed strategy for the hydrodecarbonylation of aliphatic aldehydes. Mechanistic studies highlight chlorine radical formation via Ligand-to-Metal Charge Transfer (LMCT) from in situ generated BiIIICl52-. After C(sp2)-H abstraction by the chlorine radical, decarbonylation followed by Hydrogen Atom Transfer (HAT) furnishes the desired products. Deuterium-labeling studies confirm that water serves as the hydrogen source. The reaction demonstrates excellent functional-group tolerance, including substrates bearing complex, drug-like motifs.
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