Electrochemical Decarbonylative Aminosulfonylation of Alkynes with Sulfinates and N-(Formyl)anilides

Rajeshwar Reddy Aleti; Alexey A Festa; Olga A Storozhenko; Vladimir L Bondarev; Oleg O Segida; Stanislav A Paveliev; Victor B Rybakov; Alexey V Varlamov; Leonid G Voskressensky

doi:10.1021/acs.orglett.2c03985

Electrochemical Decarbonylative Aminosulfonylation of Alkynes with Sulfinates and N-(Formyl)anilides

Org Lett. 2022 Dec 23;24(50):9337-9341. doi: 10.1021/acs.orglett.2c03985. Epub 2022 Dec 14.

Authors

Rajeshwar Reddy Aleti¹, Alexey A Festa¹, Olga A Storozhenko¹, Vladimir L Bondarev¹, Oleg O Segida², Stanislav A Paveliev², Victor B Rybakov³, Alexey V Varlamov¹, Leonid G Voskressensky¹

Affiliations

¹ Organic Chemistry Department, Science Faculty, Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya st., 6, Moscow 117198, Russia.
² N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, 47 Leninsky Prospect, Moscow 119991, Russian Federation.
³ Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory, 1-3, Moscow 119991, Russia.

PMID: 36516277
DOI: 10.1021/acs.orglett.2c03985

Abstract

An unprecedented electrochemical three-component reaction of phenylacetylene, sulfinate, and N-(formyl)anilide was discovered. The transformation occurs in an undivided cell with a graphite anode and cathode in DMF in the presence of tetrabutylammonium iodide as an electrolyte. The addition of silver(I) oxide and catalytic amounts of iodine facilitated the reaction significantly. The transformation was also carried out under photoredox-catalyzed conditions.