Electrochemical Aziridination by Alkene Activation Using a Sulfamate as the Nitrogen Source

Jin Li; Wenhao Huang; Jingzhi Chen; Lingfeng He; Xu Cheng; Guigen Li

doi:10.1002/anie.201801106

Electrochemical Aziridination by Alkene Activation Using a Sulfamate as the Nitrogen Source

Angew Chem Int Ed Engl. 2018 May 14;57(20):5695-5698. doi: 10.1002/anie.201801106. Epub 2018 Apr 20.

Authors

Jin Li¹, Wenhao Huang¹, Jingzhi Chen¹, Lingfeng He¹, Xu Cheng^{1

2

3}, Guigen Li^{1

4}

Affiliations

¹ Institute of Chemistry and Biomedical Sciences, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, National Demonstration Center for Experimental Chemistry Education, Nanjing University, Nanjing, 210023, China.
² State Key Laboratory Cultivation Base for TCM Quality and Efficacy, Nanjing University of Chinese Medicine, Nanjing, China.
³ State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin, China.
⁴ Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX, USA.

PMID: 29624835
DOI: 10.1002/anie.201801106

Abstract

The first direct aziridination of triaryl-substituted alkenes was achieved by means of an electrochemical process that could extend to multisubstituted styrenes. Specifically, hexafluoroisopropanol sulfamate was used as a nucleophilic nitrogen source. Mechanistic experiments suggest that this electrochemical process proceeds by stepwise formation of two C-N bonds through reactions between cationic carbon species and the sulfamate.

Keywords: alkenes; aziridines; electrochemistry; radicals; synthetic methods.

Publication types

Research Support, Non-U.S. Gov't