1. Electrocatalytic Minisci Acylation Reaction of N-Heteroarenes Mediated by NH4I
- Author
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Kun Xu, Yang-Ye Jiang, Qing-Qing Wang, Yong-Guo Liu, Baoguo Sun, and Cheng-Chu Zeng
- Subjects
010405 organic chemistry ,Organic Chemistry ,010402 general chemistry ,Electrochemistry ,01 natural sciences ,Biochemistry ,Combinatorial chemistry ,0104 chemical sciences ,Acylation ,chemistry.chemical_compound ,chemistry ,Functional group ,Surface modification ,Organic chemistry ,lipids (amino acids, peptides, and proteins) ,Carboxylate ,Physical and Theoretical Chemistry ,Cyclic voltammetry ,Oxidative decarboxylation ,Redox catalyst - Abstract
An electrochemical C–H acylation of electron-deficient N-heteroarenes with α-keto acids is reported. This first electrochemical Minisci acylation reaction proceeded using NH4I as a redox catalyst. A broad N-heteroarene scope and high functional group tolerance are observed. Selective monoacylation of N-heteroarenes is achieved via control of acyl radical at a low concentration. The results of cyclic voltammetry and control experiments disclose that the electrogenerated I2 is likely the active species to initiate the oxidative decarboxylation of carboxylate anion via an acyl hypoiodite intermediate. The electrochemical Minisci acylation provides a straightforward approach for the late-stage functionalization of pharmacophores.
- Published
- 2017
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