Sulfonyl fluoride synthesis via visible-light-mediated fluorosulfonylation of thianthrenium salts DOI
Lingling Shan,

Zhanhu Ma,

Caiyun Ou

et al.

Synthetic Communications, Journal Year: 2023, Volume and Issue: 53(21), P. 1784 - 1798

Published: Aug. 22, 2023

AbstractA visible-light-mediated fluorosulfonylation reaction of thianthrenium salts has been developed to prepare various sulfonyl fluorides with 1,4-diazabicyclo [2.2.2] octane bis (sulfur dioxide) (DABSO) as source and cheap KHF2 fluorine based on radical sulfur dioxide insertion fluorination strategy. This operationally simple protocol proceeds high functional-group tolerance under mild conditions.Keywords: Fluorosulfonylationthianthrenium saltsvisible-light-mediated Disclosure statementNo potential conflict interest was reported by the author(s).Additional informationFundingThe authors gratefully acknowledge financial support from National Natural Science Foundation China [No. 21871283], project Technology Commission Shanghai Municipality in [21010503800], Key Laboratory Organofluorine Chemistry, Institute Organic Chinese Academy Sciences, Engineering Research Center Green Fluoropharmaceutical Technology, Technology.

Language: Английский

Sulfur fluoride exchange DOI Open Access
Joshua A. Homer,

Long Xu,

Namitharan Kayambu

et al.

Nature Reviews Methods Primers, Journal Year: 2023, Volume and Issue: 3(1)

Published: Aug. 3, 2023

Language: Английский

Citations

53
Linkage Chemistry of S(VI) Fluorides DOI

Daming Zeng,

Wei‐Ping Deng, Xuefeng Jiang

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(33)

Published: March 24, 2023

Sulfur(VI)-fluoride exchange linkage as a next generation of click chemistry was introduced by Sharpless and coworkers in 2014. Distinguished from CuAAC, the SuFEx reaction proceeds under metal-free conditions, reactive linkers are variable, enabling access to diverse class compounds. Therein, series emerged has been widely prevalent fields. The SVI -F bond comparison -Cl features excellent stability chemoselectivity. primarily involves formation S-O S-N bonds via commercially available phenols amines, yet less study on C-SuFEx linkage. This review will focus three types for comprising S-O, S-N, S-C bonds, we hope provide practical guidance chemistry.

Language: Английский

Citations

38
Recent Advances in Developing Radical Methods for the Synthesis of Aliphatic Sulfonyl Fluorides DOI

Lu Lin,

Guanhua Pei,

Zhong‐Yan Cao

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(23)

Published: May 25, 2024

Abstract Sulfonyl fluorides have widespread applications in many fields, including organic synthesis, chemical biology, drug discovery and materials science. In particular, the past decade, a number of aliphatic sulfonyl been identified showing various biological activities. These appealing features brought about significant advancement developing synthetic methods to access fluorides. this review, we will discuss recent developments radical approaches for synthesis

Language: Английский

Citations

11
Desmethyl SuFEx-IT: SO2F2-Free Synthesis and Evaluation as a Fluorosulfurylating Agent DOI Creative Commons
Jan Bertram, Felix Neumaier, Boris D. Zlatopolskiy

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(6), P. 3821 - 3833

Published: Feb. 22, 2024

Access to SuFExable compounds was remarkably simplified by introduction of the solid FO2S-donor SuFEx-IT. However, published process for preparation this reagent relies on use sulfuryl fluoride (SO2F2), which is difficult obtain and highly toxic. Herein, we disclose a simple protocol SO2F2-free, hectogram-scale analogous desmethyl SuFEx-IT from inexpensive starting materials. The prepared in high (85%) total yield without chromatographic purification steps. In addition, demonstrate utility successful series fluorosulfates sulfamoyl fluorides excellent yields. As such, our work recognizes as valuable alternative common FO2S-donors enables cost-efficient access substrates SuFEx click chemistry.

Language: Английский

Citations

8
Recent advances in photochemical and electrochemical strategies for the synthesis of sulfonyl fluorides DOI
Yu Zheng, Wenguang Lu,

Tianting Ma

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(1), P. 217 - 235

Published: Nov. 14, 2023

This review summarizes the latest achievements in photochemical and electrochemical strategies for synthesis of sulfonyl fluorides focuses on novel features proposed mechanisms.

Language: Английский

Citations

19
FSO2 Radical-Initiated Tandem Addition Reaction of Two Different Olefins: A Facile Access to Multifunctional Aliphatic Sulfonyl Fluorides DOI

Na Yang,

Chenxi Mao,

Honghai Zhang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(24), P. 4478 - 4482

Published: June 12, 2023

Multicomponent reactions represent a powerful method for building complex molecules from structurally simple starting materials. Herein, we report novel three-component radical–polar crossover reaction involving tandem addition of two different olefins, which is initiated by the selective fluorosulfonyl radicals to alkyl alkenes. This process provides facile and effective access multiple functionalized aliphatic sulfonyl fluoride molecules. Further transformation products also demonstrated.

Language: Английский

Citations

17
Covalent hits and where to find them DOI Creative Commons
Simon C. C. Lucas, J. Henry Blackwell, Sarah H. Hewitt

et al.

SLAS DISCOVERY, Journal Year: 2024, Volume and Issue: 29(3), P. 100142 - 100142

Published: Jan. 25, 2024

Covalent hits for drug discovery campaigns are neither fantastic beasts nor mythical creatures, they can be routinely identified through electrophile-first screening using a suite of different techniques. These include biophysical and biochemical methods, cellular approaches, DNA-encoded libraries. Employing best practice, however, is critical to success. The purpose this review look at state the art covalent hit identification, how identify from library select compounds medicinal chemistry programmes.

Language: Английский

Citations

6
Modular synthesis of functional libraries by accelerated SuFEx click chemistry DOI Creative Commons
Joshua A. Homer, Rebecca A. Koelln, Andrew S. Barrow

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(11), P. 3879 - 3892

Published: Jan. 1, 2024

The Accelerated SuFEx Click Chemistry (ASCC) protocol, adapted to a 96-well plate format, has been applied the late-stage derivatization of bioactive molecules and array synthesis anticancer agents, showcasing its potential for drug discovery.

Language: Английский

Citations

6
Aliphatic Sulfonyl Fluoride Synthesis via Decarboxylative Fluorosulfonylation of Hypervalent Iodine(III) Carboxylates DOI

Caiyun Ou,

Yinxia Cai,

Yuyang Ma

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(36), P. 6751 - 6756

Published: Sept. 1, 2023

We disclose herein a photocatalytic decarboxylative fluorosulfonylation reaction of various hypervalent iodine(III) carboxylates in combination with 1,4-diazabicyclo[2.2.2]octane–bis(sulfur dioxide) adduct as sulfonyl source and KHF2 desirable fluorine via radical sulfur dioxide insertion fluorination strategy. A one-pot carboxylic acids mediated by PhI(OAc)2 was realized, well. Notably, this transformation can be performed under heating conditions without the need for catalysts.

Language: Английский

Citations

15
Aminofluorosulfonylation of β,γ-Unsaturated Hydrazones with Sulfur Dioxide and N-Fluorobenzenesulfonimide: Accessing Pyrazoline-Functionalized Aliphatic Sulfonyl Fluorides DOI

Zhi-Min Yan,

Qi Lin,

Tong-Yang Cao

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(21), P. 3910 - 3915

Published: May 24, 2023

An efficient aminofluorosulfonylation strategy was developed for the synthesis of various pyrazoline-functionalized aliphatic sulfonyl fluorides using β,γ-unsaturated hydrazones with sulfur dioxide and NFSI as starting materials under mild conditions. The fluoride products could be successfully transformed into corresponding sulfonate esters amides via sulfur(VI) exchange (SuFEx) click reactions. Preliminary mechanistic investigations demonstrate that reaction operates through a radical cyclization/SO2 insertion/fluorination cascade process.

Language: Английский

Citations

13