Photoredox catalysis has gained considerable attention in recent years due to the ability to perform selective single-electron transformations under mild conditions. While the field has been predominantly focused on the use of transition metal photosensitizers, the use of organic molecules as photocatalysts has been gaining interest due to being metal-free alternatives and exhibiting unique reactivities. Herein, we describe our initial investigation into the use of an electron-rich carbazole as a photocatalyst in the in both the C–H arylation of furan and n-butyl vinyl ether. For both reactions, 2-chlorobenzonitrile is used as the aryl substrate. In the arylation of furan, the reaction mixture is currently being analyzed by isolating and characterizing the products of the reaction. In the arylation of n-butyl vinyl ether, initial results suggest the presence of an aldehyde product in the mixture instead of the arylated n-butyl vinyl ether. More work is currently being conducted to determine the structure of the aldehyde product and to propose a possible mechanistic pathway to the formation of the product.

Carbazole derivatives as photocatalysts in the C–H arylation of furan and n-butyl vinyl ether

ACS Spring Meeting 2021

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