Electrochemical tandem cyclization to access sulfonylated fused sultams via SO2 insertion with sodium metabisulfite

An electrochemical three-component transformation between N-cyanamide alkene, Na2S2O5 and sulfonyl hydrazide is described, through which various sulfonylated fused sultams were prepared in a sustainable and modular fashion. In this process, cost-effective and easy-to-handle sodium metabisulfite was...

Full description

Saved in:
Bibliographic Details
Published inORGANIC CHEMISTRY FRONTIERS Vol. 10; no. 3; pp. 705 - 711
Main Authors Sun, Yun-Hai, Li, Cheng-Jing, Xi, Ji-Ming, Wei, Zhong-Lin, Liao, Wei-Wei
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 31.01.2023
Royal Society of Chemistry
Subjects
Chemistry
Chemistry, Organic
Electrochemistry
Electrolysis
Organic chemistry
Physical Sciences
Science & Technology
Sodium
Sodium metabisulfite
Substrates
Sulfonamides
Sulfur dioxide
SULFONAMIDES
DABCO-CENTER-DOT(SO2)
ACIDS
DABSO
SULFUR-DIOXIDE
AMINOSULFONYLATION
Online AccessGet full text

Cover

More Information
Summary:An electrochemical three-component transformation between N-cyanamide alkene, Na2S2O5 and sulfonyl hydrazide is described, through which various sulfonylated fused sultams were prepared in a sustainable and modular fashion. In this process, cost-effective and easy-to-handle sodium metabisulfite was employed as a SO2 surrogate to form N-S and S-C bonds for the construction of fused sultams in an undivided electrolysis cell without a supporting electrolyte. The broad substrate scope, available reaction components and sustainable reaction conditions enabled this electrochemical method to efficiently broaden the chemical space for the construction of cyclic sulphonamides.
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/d2qo01821g