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Photocatalytic (Hetero)Arylation of C(sp3)–H Bonds with Carbon Nitride

preprint
submitted on 31.10.2020, 06:34 and posted on 02.11.2020, 09:52 by Saikat Das, Kathiravan Murugesan, GONZALO JAVIER VILLEGAS RODRIGUEZ, Jaspreet Kaur, Joshua Barham, Aleksandr Savateev, Markus Antonietti, Burkhard Koenig
Polymeric 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 sp3 C−H bonds via a combination of hydrogen atom transfer and nickel catalysis. Our protocol has a broad synthetic scope (>70 examples including late-stage modification of densely functionalized bio-active molecules), is operationally simple, and shows high chemo- and regioselectivity. 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. Additionally, mechanistic investigations indicate that an unprecedented energy transfer process (EnT) from the organic semiconductor to the nickel complex is operating.

History

Email Address of Submitting Author

burkhard.koenig@chemie.uni-regensburg.de

Institution

University of Regensburg

Country

Germany

ORCID For Submitting Author

0000-0002-6131-4850

Declaration of Conflict of Interest

The authors declare no conflicts of interest.

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