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  • Title: Organocatalytic C-H Functionalization of Simple Alkanes.
    Author: Su F, Lu F, Tang K, Lv X, Luo Z, Che F, Long H, Wu X, Chi YR.
    Journal: Angew Chem Int Ed Engl; 2023 Nov 06; 62(45):e202310072. PubMed ID: 37731165.
    Abstract:
    The direct functionalization of inert C(sp3 )-H bonds to form carbon-carbon and carbon-heteroatom bonds offers vast potential for chemical synthesis and therefore receives increasing attention. At present, most successes come from strategies using metal catalysts/reagents or photo/electrochemical processes. The use of organocatalysis for this purpose remains scarce, especially when dealing with challenging C-H bonds such as those from simple alkanes. Here we disclose the first organocatalytic direct functionalization/acylation of inert C(sp3 )-H bonds of completely unfunctionalized alkanes. Our approach involves N-heterocyclic carbene catalyst-mediated carbonyl radical intermediate generation and coupling with simple alkanes (through the corresponding alkyl radical intermediates generated via a hydrogen atom transfer process). Unreactive C-H bonds are widely present in fossil fuel feedstocks, commercially important organic polymers, and complex molecules such as natural products. Our present study shall inspire a new avenue for quick functionalization of these molecules under the light- and metal-free catalytic conditions.
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