Journal
ACS CATALYSIS
Volume 11, Issue 3, Pages 1593-1603Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.0c05694
Keywords
heterogeneous photocatalysis; carbon nitride; hydrogen atom transfer; C(sp(3))-H arylation; dual photo nickel; drug molecule functionalization
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Funding
- German Science Foundation (DFG) [KO 1537/18-1]
- European Research Council (ERC) under the European Union's Horizon 2020 Research and Innovation Programme [741623]
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Graphitic carbon nitride materials have shown potential in synthetic photocatalysis for direct arylation of C(sp(3))-H bonds, with a broad synthetic scope and high selectivity. The unique energy-transfer process (EnT) from the organic semiconductor to the nickel complex enables diverse applications, including late-stage functionalization of drugs.
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(sp(3))-H bonds, remains underexplored. Herein, we report mesoporous graphitic carbon nitride (mpg-CN as a heterogeneous organic semiconductor photocatalyst for direct arylation of C(sp(3))-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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