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  • Title: Mesoionic Carbene-Catalyzed Formyl Alkylation of Aldehydes.
    Author: Liu C, Zhang Z, Zhao LL, Bertrand G, Yan X.
    Journal: Angew Chem Int Ed Engl; 2023 Jun 12; 62(24):e202303478. PubMed ID: 37070460.
    Abstract:
    Ketones are among the most useful functional groups in organic synthesis, and they are commonly encountered in a broad range of compounds with various applications. Herein, we describe the mesoionic carbene-catalyzed coupling reaction of aldehydes with non-activated secondary and even primary alkyl halides. This metal-free method utilizes deprotonated Breslow intermediates derived from mesoionic carbenes (MICs), which act as super electron donors and induce the single-electron reduction of alkyl halides. This mild coupling reaction has a broad substrate scope and tolerates many functional groups, which allows to prepare a diversity of simple ketones as well as bio-active molecules by late-stage functionalization.
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