Electron Donor–Acceptor Complex Enabled Cyclization/Sulfonylation Cascade of N-Heterocycles with Thianthrenium Salts DOI

Zhengjun He,

Zhi Li,

Shuo Lai

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(31), P. 6652 - 6657

Published: July 26, 2024

We report a visible-light-promoted cyclization/sulfonylation cascade of N-heterocycles with thianthrenium salts using DABSO as the SO2 surrogate. This method features excellent functional group tolerance, wide substrate scope, and late-stage elaboration bioactive relevant molecules. Mechanistic investigations reveal that photoactive electron donor–acceptor (EDA) complexes between DABCO are capable generation aryl radicals, which induce following insertion by attacking DABSO, thus triggering key radical cyclization step.

Language: Английский

Electrochemical multi-component reaction of potassium metabisulfite with alkenes and alcohols enabling synthesis of sulfonate esters DOI
Jiang Liu, Jingcheng Xu, Haibo Mei

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(16), P. 6113 - 6118

Published: Jan. 1, 2022

An electrochemical sulfur dioxide insertion reaction of alkenes and alcohols with potassium metabisulfite as the surrogate has been developed, which provides a green efficient method for preparation sulfonate esters.

Language: Английский

Citations

29
Recent advances in the synthesis of cyclic sulfinic acid derivatives (sultines and cyclic sulfinamides) DOI
Yongxin Zhang, Helian Li, Xiaoxiao Yang

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(42), P. 6272 - 6285

Published: Jan. 1, 2023

This feature article discusses the state-of-play of cyclic sulfinic acid derivative (sultines and sulfinamides) formation.

Language: Английский

Citations

22
Multicomponent Reactions Based on SO2 Surrogates: Recent Advances DOI
Gang Chen, Zhong Lian

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(25)

Published: April 25, 2023

Abstract Compounds containing sulfonyl‐derived functional groups have received intensive attention owing to their widespread applications in life science, pharmaceuticals and materials science. To access this type of compounds, the multi‐component sulfonylation reactions relying on sulfur dioxide (SO 2 ) insertion strategy emerged as novel attractive approaches past decade. The utilization SO surrogates for multicomponent (MCRs) improved reaction flexibility step economy. Moreover, some advances been achieved challenging but practical asymmetric MCRs construction high value‐added chiral sulfones. This review aims summarize progress made involving from 2019 2022, point out potentials challenges field.

Language: Английский

Citations

22
Multicomponent Sulfonylation of Alkenes to Access β-Substituted Arylsulfones DOI

Kai‐Yi Zhang,

Fang Long,

Chuan‐Chong Peng

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(6), P. 3772 - 3780

Published: March 6, 2023

A novel multicomponent sulfonylation of alkenes is described for the assembly various β-substituted arylsulfones using cheap and easily available K2S2O5 as a sulfur dioxide source. Of note, procedure does not need any extra oxidants metal catalysts exhibits relatively wide substrate scope good functional group compatibility. Mechanistically, an initial arylsulfonyl radical formed involving insertion with aryl diazonium salt, followed by alkoxyarylsulfonylation or hydroxysulfonylation alkenes.

Language: Английский

Citations

17
Electron Donor–Acceptor Complex Enabled Cyclization/Sulfonylation Cascade of N-Heterocycles with Thianthrenium Salts DOI

Zhengjun He,

Zhi Li,

Shuo Lai

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(31), P. 6652 - 6657

Published: July 26, 2024

We report a visible-light-promoted cyclization/sulfonylation cascade of N-heterocycles with thianthrenium salts using DABSO as the SO2 surrogate. This method features excellent functional group tolerance, wide substrate scope, and late-stage elaboration bioactive relevant molecules. Mechanistic investigations reveal that photoactive electron donor–acceptor (EDA) complexes between DABCO are capable generation aryl radicals, which induce following insertion by attacking DABSO, thus triggering key radical cyclization step.

Language: Английский

Citations

8