Generation of Sulfamoyl Radical for the Modular Synthesis of Sulfonamides DOI

Haiping Lv,

Xinzhou Chen, Xuemei Zhang

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(9), P. 6513 - 6524

Published: April 13, 2024

Efficient synthesis of sulfonamides has long been pursued by chemists due to their frequent occurrence in pharmaceuticals, especially anti-inflammatory medicines. The traditional assembly from sulfonyl chlorides and amines, as well the recently developed one-step involving sulfur dioxide, still faces challenges such poor substrate compatibility and/or stringent reaction conditions. Herein, we present a strategy for situ generation sulfamoyl radicals modular both alkenyl alkyl with wide applicability (>100 examples), mild conditions, easily accessible starting materials. This method is successfully applied late-stage modification drug molecules (23 molecule naratriptan, 15N-labeling sulfonamides.

Language: Английский

Sulfonyl fluorides as targets and substrates in the development of new synthetic methods DOI
Terry Shing‐Bong Lou, Michael C. Willis

Nature Reviews Chemistry, Journal Year: 2022, Volume and Issue: 6(2), P. 146 - 162

Published: Jan. 19, 2022

Language: Английский

Citations

185
Uniformly Controlled Treble Boundary Using Enriched Adsorption Sites and Accelerated Catalyst Cathode for Robust Lithium–Sulfur Batteries DOI

Rongrong Chu,

Thanh Tuan Nguyen,

Yanqun Bai

et al.

Advanced Energy Materials, Journal Year: 2022, Volume and Issue: 12(9)

Published: Jan. 13, 2022

Abstract Rechargeable lithium–sulfur batteries (LSBs) are recognized as a promising candidate for next‐generation energy storage devices because of their high theoretical specific capacity and density. However, the insulating sulfur, Li 2 S /Li S, shuttling effect order lithium polysulfides (LiPSs) hinder its practical applications. Herein, heterostructure is explored to enhance conversion reaction kinetics adsorption ability LiPSs. By rationally designing conductive carbon framework polar metal sites, both experimental results show strong abilities dissolved LiPSs promote rate. A CoSe /Co 3 O 4 @NC‐CNT/S cathode shows an excellent rate performance (≈1457 mAh g −1 at 0.1 C still retains ≈688 5 C). When performing charge–discharge in long‐term stability C, delivers initial ≈780 ≈602 after 500 cycles with Coulombic efficiency ≈95.4%. Remarkably, battery can entirely operate even very sulfur loading ≈10.1 mg cm −2 lean electrolyte condition. This work emphasizes new strategy design heterostructures that encourage industrial application LSBs.

Language: Английский

Citations

145
The Emerging Applications of Sulfur(VI) Fluorides in Catalysis DOI Creative Commons
Cayo Lee,

Alina J. Cook,

Jonathan E. Elisabeth

et al.

ACS Catalysis, Journal Year: 2021, Volume and Issue: 11(11), P. 6578 - 6589

Published: May 19, 2021

The past decade has witnessed remarkable growth of catalytic transformations in organic sulfur(VI) fluoride chemistry. This Perspective concentrates exclusively on foundational examples that utilize strategies to synthesize and react S(VI) fluorides. Key mechanistic studies aim provide insight toward future systems are emphasized.

Language: Английский

Citations

122
The importance of sulfur-containing motifs in drug design and discovery DOI
Muhamad Mustafa, Jean‐Yves Winum

Expert Opinion on Drug Discovery, Journal Year: 2022, Volume and Issue: 17(5), P. 501 - 512

Published: Feb. 23, 2022

Sulfur-containing functional groups are privileged motifs that occur in various pharmacologically effective substances and several natural products. Various functionalities found with a sulfur atom at diverse oxidation states, as illustrated by thioether, sulfoxide, sulfone, sulfonamide, sulfamate, sulfamide functions. They valuable scaffolds the field of medicinal chemistry part large array approved drugs clinical candidates.Herein, authors review current research on development organosulfur-based drug discovery. This article also covers details their roles new lead compounds reported literature over past five years 2017-2021.Given its prominent role importance discovery, has attracted continuing interest been used design demonstrate variety biological pharmacological feature activities. Overall, sulfur's continues to grow. However, many remain underused small-molecule discovery deserve special attention armamentarium for treating diseases. Research efforts still required synthetic methodology direct access these functions late-stage functionalization.

Language: Английский

Citations

120
Advances in the construction of diverse SuFEx linkers DOI Creative Commons

Daming Zeng,

Weiping Deng, Xuefeng Jiang

et al.

National Science Review, Journal Year: 2023, Volume and Issue: 10(6)

Published: April 29, 2023

Abstract Sulfur fluoride exchange (SuFEx), a new generation of click chemistry, was first presented by Sharpless, Dong and co-workers in 2014. Owing to the high stability yet efficient reactivity SVI–F bond, SuFEx has found widespread applications organic synthesis, materials science, chemical biology drug discovery. A diverse collection linkers emerged, involving gaseous SO2F2 SOF4 hubs; SOF4-derived iminosulfur oxydifluorides; O-, N- C-attached sulfonyl fluorides sulfonimidoyl fluorides; novel sulfondiimidoyl fluorides. This review summarizes progress these connectors, with an emphasis on analysing advantages disadvantages synthetic strategies connectors based concept, it is expected be beneficial researchers rapidly correctly understand this field, thus inspiring further development chemistry.

Language: Английский

Citations

69
Emerging Building Blocks for Medicinal Chemistry: Recent Synthetic Advances DOI
Oleksandr O. Grygorenko, Dmitriy M. Volochnyuk, Bohdan V. Vashchenko

et al.

European Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 2021(47), P. 6478 - 6510

Published: Sept. 8, 2021

Abstract Current medicinal chemistry relies heavily on the quality of building blocks, i. e. reagents used to introduce chemical diversity into target molecules. The last decade witnessed an emergence many novel (or well‐overlooked old) chemotypes for drug discovery, which is related adapting new synthetic methodologies, designing sp 3 ‐enriched bioisosteres, paying attention previously underrated even unwanted) structural motifs, or combination thereof. In this review with 532 references, a survey selected that emerged recently in provided, focus synthesis corresponding blocks. Thus, saturated (hetero)aliphatic boronates, sulfonyl fluorides, sulfinates, non‐classical benzene isosteres, bicyclic morpholine/piperidine/piperazine analogs, as well gem ‐difluorinated cycloalkanes (as example emerging fluorinated motifs) are discussed.

Language: Английский

Citations

94
Accelerated SuFEx Click Chemistry For Modular Synthesis** DOI
Christopher J. Smedley, Joshua A. Homer, Timothy L. Gialelis

et al.

Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 61(4)

Published: Nov. 10, 2021

Abstract SuFEx click chemistry is a powerful method designed for the selective, rapid, and modular synthesis of functional molecules. Classical reactions form stable S−O linkages upon exchange S−F bonds with aryl silyl‐ether substrates, while near‐perfect in their outcome, are sometimes disadvantaged by relatively high catalyst loadings prolonged reaction times. We herein report development accelerated (ASCC), an improved efficient catalytic coupling alkyl alcohols range SuFExable hubs. demonstrate Barton's hindered guanidine base (2‐tert‐butyl‐1,1,3,3‐tetramethylguanidine; BTMG) as superb that, when used synergy silicon additive hexamethyldisilazane (HMDS), yields bond single step; often within minutes. The combination BTMG HMDS reagents allows low 1.0 mol % and, congruence click‐principles, provides scalable that safe, efficient, practical synthesis. ASSC expands number accessible products will find significant application organic synthesis, medicinal chemistry, chemical biology, materials science.

Language: Английский

Citations

88
Photoredox catalytic radical fluorosulfonylation of olefins enabled by a bench-stable redox-active fluorosulfonyl radical precursor DOI Creative Commons
Peng Wang, Honghai Zhang, Xingliang Nie

et al.

Nature Communications, Journal Year: 2022, Volume and Issue: 13(1)

Published: June 11, 2022

Abstract Sulfonyl fluorides have attracted considerable and growing research interests from various disciplines, which raises a high demand for novel effective methods to access this class of compounds. Radical flurosulfonylation is recently emerging as promising approach the synthesis sulfonyl fluorides. However, scope applicable substrate reaction types are severely restricted by limited known radical reagents. Here, we introduce solid state, redox-active type fluorosulfonyl reagents, 1-fluorosulfonyl 2-aryl benzoimidazolium triflate (FABI) salts, enable fluorosulfonylation olefins under photoredox conditions. In comparison with precursor, gaseous FSO 2 Cl, FABI salts bench-stable, easy handle, affording yields in before challenging substrates. The advantage FABIs further demonstrated development an alkoxyl-fluorosulfonyl difunctionalization olefins, forges facile useful β-alkoxyl related compounds, would thus benefit study context chemical biology drug discovery future.

Language: Английский

Citations

64
Divergent sulfur(VI) fluoride exchange linkage of sulfonimidoyl fluorides and alkynes DOI

Daming Zeng,

Yinhao Ma,

Weiping Deng

et al.

Nature Synthesis, Journal Year: 2022, Volume and Issue: 1(6), P. 455 - 463

Published: May 9, 2022

Language: Английский

Citations

62
Electrochemical Synthesis of β-Keto Sulfonyl Fluorides via Radical Fluorosulfonylation of Vinyl Triflates DOI
Qingyuan Feng,

Yuanyuan Fu,

Yu Zheng

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(20), P. 3702 - 3706

Published: May 17, 2022

Electrochemical synthesis of versatile β-keto sulfonyl fluorides is accomplished by radical fluorosulfonylation vinyl triflates with FSO2Cl as the fluorosulfonyl source. This electroreductive protocol uses inexpensive graphite felt electrodes, thus avoiding use a sacrificial anode. Moreover, this protocol, featuring metal-free, mild conditions and easy scalability, allows expedient access to valuable from readily available precursors, well cyclic ones that are otherwise inaccessible using prior methods.

Language: Английский

Citations

39