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Abstract:
An electrochemical CH acylation of electron-deficient Nheteroarenes with a-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 voltametry and control experiments disclose that the electrogenerated I-2 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.
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ORGANIC LETTERS
ISSN: 1523-7060
Year: 2017
Issue: 20
Volume: 19
Page: 5517-5520
5 . 2 0 0
JCR@2022
ESI Discipline: CHEMISTRY;
ESI HC Threshold:212
CAS Journal Grade:1
Cited Count:
WoS CC Cited Count: 137
SCOPUS Cited Count: 131
ESI Highly Cited Papers on the List: 0 Unfold All
WanFang Cited Count:
Chinese Cited Count:
30 Days PV: 5
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