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Formal β-C-H Arylation of Aldehydes and Ketones by Cooperative Nickel and Photoredox Catalysis.

ABSTRACT: α-C-H-functionalization of ketones and aldehydes has been intensively explored in organic synthesis. The functionalization of unactivated β-C-H bonds in such carbonyl compounds is less well investigated and developing a general method for their β-C-H arylation remains challenging. Herein we report a method that uses cooperative nickel and photoredox catalysis for the formal β-C-H arylation of aldehydes and ketones with (hetero)aryl bromides. The method features mild conditions, remarkable scope and wide functional group tolerance. Importantly, the introduced synthetic strategy also allows the β-alkenylation, β-alkynylation and β-acylation of aldehydes under similar conditions. Mechanistic studies revealed that this transformation proceeds through a single electron oxidation/Ni-mediated coupling/reductive elimination cascade.

SUBMITTER: Liu K

PROVIDER: S-EPMC9400853 | biostudies-literature | 2022 Aug

REPOSITORIES: biostudies-literature

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Formal β-C-H Arylation of Aldehydes and Ketones by Cooperative Nickel and Photoredox Catalysis.

Liu Kun K Studer Armido A

Angewandte Chemie (International ed. in English) 20220623 31

α-C-H-functionalization of ketones and aldehydes has been intensively explored in organic synthesis. The functionalization of unactivated β-C-H bonds in such carbonyl compounds is less well investigated and developing a general method for their β-C-H arylation remains challenging. Herein we report a method that uses cooperative nickel and photoredox catalysis for the formal β-C-H arylation of aldehydes and ketones with (hetero)aryl bromides. The method features mild conditions, remarkable scope ...[more]

PMID: 35656716

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