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

Ni-catalyzed C–S bond construction and cleavage DOI
Su Huang, Ming Wang, Xuefeng Jiang

et al.

Chemical Society Reviews, Journal Year: 2022, Volume and Issue: 51(19), P. 8351 - 8377

Published: Jan. 1, 2022

This review focuses on nickel-catalyzed construction and transformation of various sulfide-containing compounds, such as sulfides, disulfides, hypervalent sulfur-containing compounds.

Language: Английский

Citations

142

Radical approaches to C–S bonds DOI
Zijun Wu, Derek A. Pratt

Nature Reviews Chemistry, Journal Year: 2023, Volume and Issue: 7(8), P. 573 - 589

Published: June 21, 2023

Language: Английский

Citations

52

A reagent to access methyl sulfones DOI Creative Commons

Yaroslav Poplavskyi,

Vasyl Ripenko,

Sergei Bova

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: Jan. 29, 2025

A chemical reagent to access methyl sulfones has been developed. Its reaction with various bis-nucleophiles leads the rapid formation of previously unknown heteroaromatic sulfones. Analogous strategy can also be used construct alkyl-, CHF2-, CF3- and even bicyclo[1.1.1]pentane-containing derivatives. These compounds have demonstrated a high potential for use in medicinal chemistry coordination chemistry. Methyl sulfone is standard polar substituent found different agro chemicals or drugs but due lack convenient efficient approaches them, are less investigated. Here authors report

Language: Английский

Citations

2

Advances in photochemical and electrochemical incorporation of sulfur dioxide for the synthesis of value-added compounds DOI Creative Commons

Stephan P. Blum,

Kamil Hofman,

Georg Manolikakes

et al.

Chemical Communications, Journal Year: 2021, Volume and Issue: 57(67), P. 8236 - 8249

Published: Jan. 1, 2021

Photosynthesis and electrosynthesis enable the “green” upcycling of SO 2 to value-added products.

Language: Английский

Citations

82

The Same Oxidation‐State Introduction of Hypervalent Sulfur via Transition‐Metal Catalysis DOI
Ming Wang, Xuefeng Jiang

The Chemical Record, Journal Year: 2021, Volume and Issue: 21(12), P. 3338 - 3355

Published: Jan. 26, 2021

Abstract Sulfonyl compounds have attracted considerable interest due to their extensive applications in drug discovery, agricultural, and material science. The access the assembly of SO 2 ‐containing via same oxidative‐state introduction hypervalent sulfur has come fore recent years. Especially, transition‐metal‐involved synthesis is most effective strategy since easy insert into metal‐carbon bonds. This review discusses application oxidation‐state under transition‐metal‐catalyzed conditions, presents according different metal catalysts synthesized diversity sulfur‐containing skeletons, including sulfonamides, sulfones, sulfinamides, sulfonyl acids fluorides.

Language: Английский

Citations

69

Sulfonylation of Aryl Halides by Visible Light/Copper Catalysis DOI

Qiuli Yan,

Wenwen Cui, Xiuyan Song

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(9), P. 3663 - 3668

Published: April 21, 2021

An efficient visible-light-assisted, copper-catalyzed sulfonylation of aryl halides with sulfinates is reported. In our protocol, a single ligand CuI photocatalyst formed in situ was used the photocatalytic transformation. Diverse organosulfones were obtained moderate to good yields. This strategy demonstrates promising approach toward synthesis diverse and useful organosulfones.

Language: Английский

Citations

68

Synthesis and perspective of organosulfur chemicals in agrochemicals DOI Creative Commons
Jiajia Yu, Xuefeng Jiang

Advanced Agrochem, Journal Year: 2022, Volume and Issue: 2(1), P. 3 - 14

Published: Dec. 21, 2022

As well known, with the increase of world population, improving agricultural production has always been great importance. Due to effective protection against pests or pathogenic bacteria and promoting growth crops, agrochemical holds vital position in modern agriculture. In this field, introducing sulfur moieties into active ingredients improve property pesticides a powerful tool for development agrochemical. Thus, efficient methods construction organosulfur scaffolds existed agrochemicals are highly desirable, which also attract considerable attentions over past few decades. Herein, we provide comprehensive introduction representative synthetic access sulfur-containing molecules frequently found utilization various sulfurizing agents, point out potential direction further development.

Language: Английский

Citations

65

Photoredox-catalyzed aminofluorosulfonylation of unactivated olefins DOI Creative Commons
Tao Zhong,

Ji-Tao Yi,

Zhida Chen

et al.

Chemical Science, Journal Year: 2021, Volume and Issue: 12(27), P. 9359 - 9365

Published: Jan. 1, 2021

A three-component aminofluorosulfonylation of unactivated alkenes has been developed by merging photocatalytic PCET with radical relay processes, affording various aliphatic sulfonyl fluorides featuring medicinally privileged heterocyclic scaffolds.

Language: Английский

Citations

63

Photoredox-Catalyzed α-Sulfonylation of Ketones from Sulfur Dioxide and Thianthrenium Salts DOI
Fu‐Sheng He,

Ping Bao,

Zhimei Tang

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(15), P. 2955 - 2960

Published: April 13, 2022

A photoredox-catalyzed sulfonylation of silyl enol ethers with DABCO·(SO2)2 and thianthrenium salts is achieved, providing diverse β-keto sulfones in moderate to good yields. This protocol features easily accessible starting materials functional group compatibility, enabling the introduction various functionalized sulfonyl groups into ketones. Furthermore, as one important industrial raw materials, methanol can be employed methyl source prepare α-methylsulfonated ketones through a intermediate for first time.

Language: Английский

Citations

63

Generation and Use of Glycosyl Radicals under Acidic Conditions: Glycosyl Sulfinates as Precursors DOI

Shiyang Xu,

Wei Zhang,

Caiyi Li

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(16)

Published: Feb. 10, 2023

We herein report a method that enables the generation of glycosyl radicals under highly acidic conditions. Key to success is design and use sulfinates as radical precursors, which are bench-stable solids can be readily prepared from commercial starting materials. This development allows installation units onto pyridine rings directly by Minisci reaction. further demonstrate utility this in late-stage modification complex drug molecules, including anticancer agent camptothecin. Experimental studies provide insight into reaction mechanism.

Language: Английский

Citations

34