Oxidase-Type C-H/C-H Coupling Using an Isoquinoline-Derived Organic Photocatalyst

Zhang, Lei and Pfund, Björn and Wenger, Oliver S. and Hu, Xile. (2022) Oxidase-Type C-H/C-H Coupling Using an Isoquinoline-Derived Organic Photocatalyst. Angewandte Chemie International Edition, 61. e202202649.

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Official URL: https://edoc.unibas.ch/88646/

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Oxidase-type oxidation is an attractive strategy in organic synthesis due to the use of O-2 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.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Anorganische Chemie (Wenger)
UniBasel Contributors:Wenger, Oliver and Pfund, Björn
Item Type:Article, refereed
Article Subtype:Research Article
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:29 Jun 2022 08:20
Deposited On:29 Jun 2022 08:20

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