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. 2024 Mar 18;63(12):e202315222.
doi: 10.1002/anie.202315222. Epub 2024 Feb 19.

Electrochemical Ni-Catalyzed Decarboxylative C(sp3 )-N Cross-Electrophile Coupling

Yue-Ming Cai  1 , Xiao-Ting Liu  1 , Lin-Lin Xu  1 , Ming Shang  1
Affiliations

Electrochemical Ni-Catalyzed Decarboxylative C(sp3 )-N Cross-Electrophile Coupling

Yue-Ming Cai et al. Angew Chem Int Ed Engl. .

Abstract

A new electrochemical transformation is presented that enables chemists to couple simple alkyl carboxylic acid derivatives with an electrophilic amine reagent to construct C(sp3 )-N bond. The success of this reaction hinges on the merging of cooperative electrochemical reduction with nickel catalysis. The chemistry exhibits a high degree of practicality, showcasing its wide applicability with 1°, 2°, 3° carboxylic acids and remarkable compatibility with diverse functional groups, even in the realm of late-stage functionalization. Furthermore, extensive mechanistic studies have unveiled the engagement of alkyl radicals and iminyl radicals; and elucidated the multifaceted roles played by i Pr2 O, Ni catalyst, and electricity.

Keywords: carboxylic acid; cross-electrophile coupling; electrochemistry; iminyl radical; late-stage functionalization.

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