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  • Title: Direct Acylation of Unactivated Alkyl Halides with Aldehydes through N-Heterocyclic Carbene Organocatalysis.
    Author: Li QZ, Zeng R, Xu PS, Jin XH, Xie C, Yang QC, Zhang X, Li JL.
    Journal: Angew Chem Int Ed Engl; 2023 Oct 02; 62(40):e202309572. PubMed ID: 37581950.
    Abstract:
    Catalytic acylation of organohalides with aldehydes is an ideal strategy for the direct synthesis of ketones. However, the utilization of unactivated alkyl halides in such a transformation remains a formidable challenge. In this study, we developed a cross-coupling reaction of aldehydes with unactivated alkyl halides through N-heterocyclic carbene catalysis. With this protocol, various ketones could be rapidly synthesized from readily available starting materials under mild conditions. This organocatalytic system was successfully applied in the late-stage functionalization of pharmaceutical derivatives. Mechanistic investigations suggest a closed-shell nucleophilic substitution mechanism for this reaction.
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