Photocatalytic (Het)arylation of C(sp3)–H Bonds with Carbon Nitride

    • Saikat Dasa
    • Kathiravan Murugesana
    • Gonzalo J. Villegas Rodrígueza
    • Jaspreet Kaura
    • Joshua. P. Barhama
    • Aleksandr Savateevb
    • Markus Antoniettib
    • Burkhard Königa
    • aFakultät für Chemie und Pharmazie, Universität Regensburg, 93040 Regensburg, Germany
    • bDepartment of Colloid Chemistry, Max-Planck Institute of Colloids and Interfaces, Research Campus Golm, 14424 Potsdam, Germany

    Graphitic carbon nitride materials have attracted significant interest in recent years and found applications in diverse light-to-energy conversions such as artificial photosynthesis, CO2 reduction, or degradation of organic pollutants. However, their utilization in synthetic photocatalysis, especially in the direct functionalization of C(sp3)–H bonds, remains underexplored. Herein, we report mesoporous graphitic carbon nitride (mpg-CN) as a heterogeneous organic semiconductor photocatalyst for direct arylation of C(sp3)–H bonds in combination with nickel catalysis. Our protocol has a broad synthetic scope (>70 examples including late-stage functionalization of drugs and agrochemicals), is operationally simple, and shows high chemo- and regioselectivities. Facile separation and recycling of the mpg-CN catalyst in combination with its low preparation cost, innate photochemical stability, and low toxicity are beneficial features overcoming typical shortcomings of homogeneous photocatalysis. Detailed mechanistic investigations and kinetic studies indicate that an unprecedented energy-transfer process (EnT) from the organic semiconductor to the nickel complex is operating.

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