The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown
Опубликована: Ноя. 8, 2024
A Pd
Язык: Английский
Angewandte Chemie, Год журнала: 2024, Номер 136(40)
Опубликована: Июнь 29, 2024
Abstract High‐throughput synthesis and screening of chemical libraries play pivotal roles in drug discovery. Click chemistry has emerged as a powerful strategy for constructing highly modular libraries. However, the development new click reactions unlocking clickable building blocks remain exceedingly challenging. Herein, we describe double‐click that enables sequential ligations widely available carboxylic acids amines with fluorosulfuryl isocyanate (FSO 2 NCO) via amidation/SuFEx (sulfur‐fluoride exchange) process. This method provides facile access to N‐fluorosulfonyl amides (RCONHSO F) N‐acylsulfamides NR′R′′) near‐quantitative yields under simple practical conditions. The robustness efficiency this double is showcased by construction 96‐well microtiter plates from large number amines. Preliminary biological activity reveals some compounds exhibit high antimicrobial activities against Gram‐positive bacterium S. aureus drug‐resistant MRSA (MIC up 6.25 μg ⋅ mL −1 ). These results provide compelling evidence potential application library an enabling technology high‐throughput medicinal chemistry.
Язык: Английский
Процитировано
1
The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(15), С. 10919 - 10928
Опубликована: Июль 16, 2024
An efficient visible-light-induced synthesis of vinyl sulfones has been accomplished via decarboxylative sulfonylation cinnamic acids using sulfonylazides,
Язык: Английский
Процитировано
1
Synthesis, Год журнала: 2024, Номер unknown
Опубликована: Сен. 5, 2024
Abstract Sulfur(VI)–fluoride exchange (SuFEx) is a second generation, metal-free click chemistry concept introduced by Sharpless in 2014. Since the introduction of concept, large variety synthetic methodologies to S(VI)-SuFEx hubs, and their derivatization with oxygen-, nitrogen-, carbon-based nucleophiles have been developed. Herein, we provide concise practical overview for preparation, SuFExability, inclusive which substituents are tolerated. The stereoselective synthesis aza-derivatives also discussed. 1 Introduction 2 Synthesis SuFEx Hubs 2.1 Sulfonyl Fluorides 2.2 Fluorosulfates 2.3 Sulfamoyl 2.4 Sulfonimidoyl 2.5 Sulfuramidimidoyl Sulfurofluoridoimidates 2.6 Sulfondiimidoyl 3 Reactivity 3.1 3.2 3.3 3.4 3.5 3.6 4 Stereochemical Considerations Chemistry 5 Conclusion Outlook
Язык: Английский
Процитировано
1
The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(13), С. 9440 - 9449
Опубликована: Июнь 14, 2024
A mild protocol for electrochemically oxidative fluorodifunctionalization of styrenes has been demonstrated. The reaction proceeds under metal, external oxidant, and catalyst free conditions, allowing tunable access to a wide variety synthetically useful fluoroalkyl derivatives, such as β-fluorosulfone/fluoromethyl, fluorothiocyanation, vinylsulfonyl derivatives. Moreover, CsF was shown be the proper fluorine source this electrochemical transformation.
Язык: Английский
Процитировано
0
Angewandte Chemie, Год журнала: 2024, Номер 136(38)
Опубликована: Июнь 26, 2024
Abstract A modular synthesis of sulfondiimidoyl fluorides—the double aza‐analogues sulfonyl fluorides—allowing variation the carbon and both nitrogen‐substituents is reported. The chemistry uses readily available organometallic reagents, commercial sulfinylamines, simple electrophiles, N‐fluorobenzenesulfonimide (NFSI), as starting materials. reactions are broad in scope, efficient, scalable. We show that fluoride products can be combined with amines to provide sulfondiimidamides, organolithium reagents sulfondiimines, reactivity these transformations modulated by N‐substituents.
Язык: Английский
Процитировано
0
Synthesis, Год журнала: 2024, Номер unknown
Опубликована: Июль 19, 2024
Abstract A novel protocol for synthesizing sulfonyl fluorides from thiols in one pot is reported. Utilizing SOCl2 and H2O2 as low-cost convenient reagents allows the direct oxidative chlorination of readily available thiol derivatives to give corresponding chlorides, with subsequent fluoride–chloride exchange mediated by KHF2 giving access desired fluorides. This transformation features mild conditions, operational simplicity high efficiency, utilizes a broad substrate scope, including variety aryl, alkyl, benzyl heteroaryl thiols.
Язык: Английский
Процитировано
0
Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(37), С. 7690 - 7695
Опубликована: Янв. 1, 2024
An organophotocatalytic approach for the site-selective sulfonylation of C(sp 2 )–H bonds anilide and quinoline amide derivatives utilizing aryl sulfonyl chlorides as a sulfonylating agent is developed.
Язык: Английский
Процитировано
0
Organic Letters, Год журнала: 2024, Номер 26(40), С. 8463 - 8467
Опубликована: Окт. 2, 2024
We present here a novel paired electrocatalysis-enabled convenient synthesis of the (
Язык: Английский
Процитировано
0
Organic Letters, Год журнала: 2024, Номер 26(42), С. 9132 - 9137
Опубликована: Окт. 16, 2024
Both fluorosulfonyl and cyano groups are important structural motifs in bioactive molecules. Herein, we report a new difunctionalization reaction of alkenes based on radicals, which allows for the introduction into unactivated one step. This transformation is enabled by merging photoredox copper catalysis, featuring visible light mild conditions, good functional group tolerance. Further products via SuFEx reactions also demonstrated.
Язык: Английский
Процитировано
0
Synthesis, Год журнала: 2024, Номер unknown
Опубликована: Окт. 21, 2024
Abstract Sulfonyl fluorides, due to their balanced potential reactivity and stability as well compatibility with biological systems, have become important synthetic intermediates building blocks in the fields of organic synthesis, drug discovery, materials science. Especially after report sulfur(VI) fluoride exchange (SuFEx) chemistry by Sharpless others, research on sulfonyl compounds related has increased significantly. This review summarizes application fluorides synthesis period 2014–2024, discussing different types reactions, including C–X bond formation (including C–C, C–N, C–F etc.), S–C formation, S–N S–O multicomponent ‘one-pot’ cyclization. 1 Introduction 2 Fluorides Applied (C, N, F) Bond Formation 3 4 5 6 Multicomponent Reactions 7 Cyclizations 8 Conclusion Perspective
Язык: Английский
Процитировано
0