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  • Title: Formal β-C-H Arylation of Aldehydes and Ketones by Cooperative Nickel and Photoredox Catalysis.
    Author: Liu K, Studer A.
    Journal: Angew Chem Int Ed Engl; 2022 Aug 01; 61(31):e202206533. PubMed ID: 35656716.
    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.
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