Electrochemical Synthesis of trans-2,3-Disubstituted Aziridines via Oxidative Dehydrogenative Intramolecular C(sp3)–H Amination

An electrochemical oxidative dehydrogenative C­(sp3)–H amination reaction to construct trans-2,3-disubstituted aziridines is reported, which avoids using external oxidants and generates only hydrogen gas as the byproduct. With KI as the mediator and electrolyte, the desired aziridines were prepared...

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Bibliographic Details
Published inOrganic letters Vol. 21; no. 23; pp. 9430 - 9433
Main Authors Wang, Huiqiao, Shi, Jianxue, Tan, Jiajing, Xu, Wenting, Zhang, Sheng, Xu, Kun
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.12.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ELECTROSYNTHESIS
ALKENES
IODINE
METAL
C-H FUNCTIONALIZATION
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Summary:An electrochemical oxidative dehydrogenative C­(sp3)–H amination reaction to construct trans-2,3-disubstituted aziridines is reported, which avoids using external oxidants and generates only hydrogen gas as the byproduct. With KI as the mediator and electrolyte, the desired aziridines were prepared in good yields in an undivided cell at room temperature. The potential value of this mild electrochemical strategy was further highlighted by the gram-scale synthesis.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b03641