Thiuram Disulfide Mediated Copper-Catalyzed C–S Cross-Coupling: Synthesis of S-Thiocarbamate Compounds DOI
Amit Saha, Sourav Mondal, D. Patra

et al.

Synlett, Journal Year: 2024, Volume and Issue: unknown

Published: July 30, 2024

Abstract Thiuram disulfides undergo a Cu(I)-catalyzed C–S cross-coupling with aryl iodides through Cu(OAc)2·H2O-assisted desulfurization to produce the S-thiocarbamate ester compounds efficiently. Various containing diverse substituents underwent smooth reaction series of cyclic and acyclic secondary amine-based thiuram under an open-air atmosphere. A probable mechanistic pathway has been suggested based on control experiments reports from literature.

Language: Английский

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

7
Visible Light-Induced Radical Cascade Functionalization of Quinoxalin-2(1H)-ones: Three-Component 1,2-Di(hetero)arylation Approach with Styrenes and Thianthrenium Salts DOI

Sudip Sau,

Shinobu Takizawa, Hun Young Kim

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(41), P. 8821 - 8826

Published: Oct. 9, 2024

The additive-free visible light-induced three-component 1,2-di(hetero)arylation of styrenes was developed using quinoxalin-2(1

Language: Английский

Citations

4
Aryl-Radical-Initiated Z-Olefin Synthesis via Synergistic Palladium and Photocatalysis DOI

Peizhi Bai,

Yue Hu, Yanwei Gu

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 7, 2025

We report a novel photocatalyzed selective functionalization of terminal olefins for the synthesis Z-olefins and cyclobutanes under mild conditions in excellent yields. A series Z-cinnamic acid derivatives, enamines, amide-containing were efficiently synthesized using this method. Mechanistic studies indicated that success reaction is based on triple radical relay strategy, anion-π interaction aryl halide activation generation, palladium controlling chemoselectivity radical, photocatalyst stereoselectivity via diradical species, respectively.

Language: Английский

Citations

0
General Electron-Donor-Acceptor Complex Mediated Thioesterification Reaction via Site-Selective C-H Functionalization using Aryl Sulfonium Salts DOI

Roshan I. Patel,

Barakha Saxena,

Anuj Sharma

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(19), P. 10265 - 10274

Published: Jan. 1, 2024

We herein describe a versatile electron–donor–acceptor (EDA) mediated thioesterification reaction using aryl sulfonium salt (acceptor) with potassium thioacid salts (donor) under visible light irradiation.

Language: Английский

Citations

3
Electron-donor-acceptor (EDA) complex-driven regioselective vicinal and oxidative geminal functionalization of alkynes† DOI

Dinabandhu Barik,

Nikita Chakraborty, Ashish Kumar Sahoo

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

A visible-light-initiated electron-donor-acceptor (EDA) complex-driven regioselective vicinal and oxidative geminal thiosulfonylation of alkynes is presented. Organic thiosulfonates act as an acceptor, producing either sulfonyl (RSO

Language: Английский

Citations

2
Pyrrolylsulfonium salts: stable, accessible and versatile pseudohalides for Stille couplings DOI Creative Commons
Jodie L. Hann, Catherine L. Lyall, Gabriele Kociok‐Köhn

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Pyrroles functionalised with a thianthrenium or diphenylsulfonium group undergo Stille couplings aryl alkynyl stannanes in good yields, avoiding the issues of instability that can hamper use analogous pyrrolyl halides.

Language: Английский

Citations

0
Thiuram Disulfide Mediated Copper-Catalyzed C–S Cross-Coupling: Synthesis of S-Thiocarbamate Compounds DOI
Amit Saha, Sourav Mondal, D. Patra

et al.

Synlett, Journal Year: 2024, Volume and Issue: unknown

Published: July 30, 2024

Abstract Thiuram disulfides undergo a Cu(I)-catalyzed C–S cross-coupling with aryl iodides through Cu(OAc)2·H2O-assisted desulfurization to produce the S-thiocarbamate ester compounds efficiently. Various containing diverse substituents underwent smooth reaction series of cyclic and acyclic secondary amine-based thiuram under an open-air atmosphere. A probable mechanistic pathway has been suggested based on control experiments reports from literature.

Language: Английский

Citations

0