Electrochemically Induced Synthesis of Sulfonylated N-Unsubstituted Enamines from Vinyl Azides and Sulfonyl Hydrazides

Electrochemically Induced Synthesis of Sulfonylated N-Unsubstituted Enamines from Vinyl Azides and Sulfonyl Hydrazides Full article

Journal

Organic Letters
ISSN: 1523-7060 , E-ISSN: 1523-7052

Output data

Year: 2020, Volume: 22, Number: 5, Pages: 1818-1824 Pages count : 7 DOI: 10.1021/acs.orglett.0c00139

Authors

Mulina Olga M. ¹ , Zhironkina Nataliya V. ^2,1 , Paveliev Stanislav A. ¹ , Demchuk Dmitry V. ¹ , Terent’ev Alexander O. ^2,1

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation
2	D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Square, 125047 Moscow, Russian Federation

Sulfonylated N-unsubstituted enamines were synthesized through a chain of chemical and electrochemical transformations via sulfonylation of vinyl azides. The disclosing of the N-unsubstituted enamines synthesis was based on a unique property of the azido group, which is its ability to eliminate the N2 molecule. Furthermore, a formal paradox is observed: a double bond reacts and a double bond is retained. Electrosynthesis proceeded in an undivided cell equipped with a graphite anode and a stainless steel cathode; NH4I was used as a supporting electrolyte.

Mulina O.M. , Zhironkina N.V. , Paveliev S.A. , Demchuk D.V. , Terent’ev A.O.
Electrochemically Induced Synthesis of Sulfonylated N-Unsubstituted Enamines from Vinyl Azides and Sulfonyl Hydrazides
Organic Letters. 2020. V.22. N5. P.1818-1824. DOI: 10.1021/acs.orglett.0c00139 WOS Scopus OpenAlex

≡ Web of science:	WOS:000518875500025
≡ Scopus:	2-s2.0-85080085909
≡ OpenAlex:	W3007465111