SO₂ClF-promoted chlorination-oxidation of 2-methylindoles: a one-step synthetic method to access 2,3-difunctionalized indoles

Abstract

A direct and one-step method for the synthesis of 3-chloro-2-formylindoles with SO2ClF is reported. This tandem system consists of double electrophilic chlorination and deprotonation, nucleophilic addition of H2O to the...

SO2ClF‐Promoted Chlorooxidation of Tryptamine Derivatives: Synthesis of 3,3‐Disubstituted Oxindoles

“…This result is consistent with our recent work on SO 2 ClF-promoted chlorination-oxidation of 2-methylindoles. [20] It is important to note that no overchlorination on the aromatic ring was observed for all cases under the current optimal conditions. Unfortunately, the present system has some limitations.…”

Radical Ring-Opening Fluorosulfonylation of Methylenecyclobutanols via Electron Donor–Acceptor Photoactivation

“…For example, para -methoxybenzylidenecyclobutanol 3a afforded chlorinated product 4a with a Z -olefin moiety in only 10 min under otherwise identical conditions, as shown in Scheme . Sulfuryl chlorofluoride functioned as an electrophilic chlorination reagent and reacted with electron-rich alkene in compound 3a through a similar pathway as the known ring-opening fluorination process . Switching the solvent from Et 2 O to THF resulted in an increase of the yield, giving product 4a in 67% yield (Scheme B).…”

“…Recently, we have shown that strong electrophilic sulfuryl chlorofluoride (FSO 2 Cl) displays significantly different reactivity from alkyl or aryl sulfonyl chlorides . It can readily form EDA complexes with weak electron donors, propargyl alcohols, to trigger the FSO 2 radical formation .…”