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Photoredox/Nickel Dual Catalysis-Enabled Aryl Formylation with 2,2-Dimethoxy-<i>N</i>,<i>N</i>-dimethylethan-1-amine as CO Source

Jie Gao, Xian‐Chen He, Yanling Liu, Pin-Pin Yao, Jianping Guan, Kai Chen, Hao‐Yue Xiang, Hua Yang

2024Organic Letters20 citationsDOI

Abstract

Herein, a dual photoredox/nickel catalyzed formylation of aryl bromide with commercially available 2,2-dimethoxy- N, N -dimethylethan-1-amine as an effective CO source has been successfully achieved, delivering a series of aromatic aldehydes in moderate to good yields. Compared with the traditional reductive carbonylation process, this newly designed synthetic protocol provides a straightforward toolbox to access aromatic aldehydes, obviating the use of carbon monoxide and stoichiometric reductants. Finally, the utility of this direct formylation reaction was demonstrated in the pharmaceutical analogue synthesis.

Topics & Concepts

FormylationChemistryCarbonylationArylAmine gas treatingCatalysisCombinatorial chemistryNickelBromideCarbon monoxideOrganic chemistryAlkylRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsCarbon dioxide utilization in catalysis