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Electrochemically Enabled Intramolecular Aminooxygenation of Alkynes via Amidyl Radical Cyclization
Author(s) -
Hou ZhongWei,
Xu HaiChao
Publication year - 2020
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201900500
Subject(s) - chemistry , electrosynthesis , radical , intramolecular force , electrochemistry , combinatorial chemistry , redox , oxygen atom , organic chemistry , molecule , electrode
Summary of main observation and conclusion An electrochemical synthesis of oxazol‐2‐ones and imidazol‐2‐ones has been developed via 5‐ exo ‐ dig cyclization of propargylic carbamates‐ and ureas‐derived amidyl radicals. The electrosynthesis relies on the dual function of 2,2,6,6‐tetramethylpiperidin‐ 1‐yl)oxyl (TEMPO) as a redox mediator for amidyl radical formation and an oxygen atom donor. The reactions are conducted under mild conditions using a simple setup and provide convenient access to functionalized oxazol‐2‐ones and imidazol‐2‐ones from readily available materials.