Work

Combined Photoredox and Carbene Catalysis for the Synthesis of γ‐Aryloxy Ketones

Year: 2021

Type: article

Abstract: -heterocyclic carbenes (NHCs) have emerged as catalysts for the construction of C-C bonds in the synthesis of substituted ketones under single-electron processes. Despite these recent reports, there still remains a need to increase the utility and practicality of these reactions by exploring new radical coupling partners. Herein, we report the synthesis of γ-aryloxyketones via combined NHC/photoredox catalysis. In this reaction, an α-aryloxymethyl radical is generated via oxidation of an aryloxymethyl potassium trifluoroborate salt, which is then added into styrene derivatives to provide a stabilized benzylic radical. Subsequent radical-radical coupling reaction with an azolium radical affords the γ-aryloxy ketone products.

Source: Advanced Synthesis & Catalysis

DOI: 10.1002/adsc.202101354

Authors: Pengzhi Wang, Keegan P. Fitzpatrick, Karl A. Scheidt

Institution: Northwestern University

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Northwestern University, National Institute of General Medical Sciences, National Institute of Diabetes and Digestive and Kidney Diseases

Awards: Kidney Therapeutics: Translating Discoveries into Prevention, Treatment and Cures for Kidney Diseases, G749739012