Abstract Oxidase‐type oxidation is an attractive strategy in organic synthesis due to the use of O2 as the terminal oxidant. Organic photocatalysis can effect metal‐free oxidase chemistry. Nevertheless, current methods are limited in reaction scope, possibly due to the lack of suitable photocatalysts. Here we report an isoquinoline‐derived diaryl ketone‐type photocatalyst, which has much enhanced absorption of blue and visible light compared to conventional diaryl ketones. This photocatalyst enables dehydrogenative cross‐coupling of heteroarenes with unactivated and activated alkanes as well as aldehydes using air as the oxidant. A wide range of heterocycles with various functional groups are suitable substrates. Transient absorption and excited‐state quenching experiments point to an unconventional mechanism that involves an excited state “self‐quenching” process to generate the N‐radical cation form of the sensitizer, which subsequently abstracts a hydrogen atom from the alkane substrate to yield a reactive alkyl radical.
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