Oxidative Cascade Sulfonylation/Cyclisation of N‐Propargylindoles with Hantzsch Esters via Sulfur Dioxide Insertion

An oxidative sulfonylation/cyclisation of N‐propargylindoles with Hantzsch esters through sulfur dioxide insertion has been developed. The method uses Na2S2O5 as sulfur dioxide source along with 4‐alkyl‐substituted Hantzsch esters as radical precursors for accessing sulfonyl radicals, and allows for...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 365; no. 12; pp. 1989 - 1994
Main Authors Sui, Jia‐Li, Fan, Jian‐Hong, Xiong, Bi‐Quan, Tang, Ke‐Wen, Liu, Yu
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 20.06.2023
Wiley Subscription Services, Inc
Subjects
4-alkyl Hantzsch esters
Chemistry
Chemistry, Applied
Chemistry, Organic
Esters
Indoles
Insertion
N-propargylindoles
Physical Sciences
Science & Technology
Sodium metabisulfite
sulfonylation
Sulfur dioxide
sulfur dioxide insertion
transition metal-free
SURROGATE
REAGENTS
sulfonylation
ONE-POT
3-COMPONENT REACTION
ALKYLATION
SULFONES
sulfur dioxide insertion
N-propargylindoles
ARYL HALIDES
transition metal-free
DABSO
4-alkyl Hantzsch esters
FIXATION
ACCESS
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Summary:An oxidative sulfonylation/cyclisation of N‐propargylindoles with Hantzsch esters through sulfur dioxide insertion has been developed. The method uses Na2S2O5 as sulfur dioxide source along with 4‐alkyl‐substituted Hantzsch esters as radical precursors for accessing sulfonyl radicals, and allows for the synthesis of 2‐sulfonated 9H‐pyrrolo[1,2‐a]indoles.
Bibliography:These authors contributed equally to this work.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202300402