Journal
ORGANIC LETTERS
Volume 19, Issue 20, Pages 5517-5520Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b02589
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Funding
- National Key Technology RD Program [2017YFB0307502, 2011BAD23B01]
- National Natural Science Foundation of China [21272021, 21472011]
- Open Project Program of Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University (BTBU)
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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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