Green and efficient synthesis of pure β-sulfonyl aliphatic sulfonyl fluorides through simple filtration in aqueous media DOI

Kang Feng,

Jianbai Wang,

Weidong Zhang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(24), P. 4967 - 4971

Published: Jan. 1, 2023

A green and efficient method for the synthesis of β-sulfonyl aliphatic sulfonyl fluorides was developed. This reaction works in aqueous media under mild environmentally benign conditions without any ligand or additive. The efficiency this is demonstrated by isolating desired products obtained through simple filtration.

Language: Английский

Visible-light-induced four-component difunctionalization of alkenes to construct phosphorodithioate-containing quinoxalin-2(1H)-ones DOI
Xiao‐Ming Chen,

Lianhui Song,

Jun Pan

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 35(11), P. 110112 - 110112

Published: June 25, 2024

Language: Английский

Citations

27
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
Multicomponent Heteroarylphosphorothiolation of Alkenes for Accessing β‐Phosphorothiolated Quinoxalinones DOI
Sha Peng, Lihua Yang,

Xiang-Qin Xu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(12), P. 2758 - 2763

Published: April 24, 2024

Abstract Herein, we present a (NH 4 ) 2 S O 8 mediated difunctionalization reaction of aryl alkenes with quinoxalinones and P(O)SH compounds. This method enables the synthesis various phosphorothioate‐containing quinoxalin‐2(1 H )‐one derivatives (46 examples) in 37–79% yields. The is compatible range functional groups easily adaptable to large‐scale synthesis. Preliminary studies suggest involvement phosphorothioate radicals these transformations.

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
Fluorosulfonylvinylation of Unactivated C(sp3)–H via Electron Donor–Acceptor Photoactivation DOI

Xueyan Zhao,

Dengfeng Chen, Shengzhen Zhu

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(17), P. 3109 - 3113

Published: April 21, 2023

An electron donor-acceptor (EDA) complex photoactivation strategy for radical fluorosulfonylation is disclosed the first time. Simply upon blue light irradiation, FSO2 can be generated efficiently under catalyst-free, base-free, and additive-free conditions, which enables facile access to 6-keto alkenylsulfonyl fluorides from readily available propargyl alcohols FSO2Cl. The fluoride motif has been showcased as a versatile SuFEx hub with diverse follow-up derivatizations.

Language: Английский

Citations

18
Radical Hydro-Fluorosulfonylation of Propargylic Alcohols via Electron Donor–Acceptor Photoactivation DOI

Yingyin Zhang,

Qingyuan Feng, Yu Zheng

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(7), P. 1410 - 1415

Published: Feb. 15, 2024

A radical hydro-fluorosulfonylation of propargyl alcohols with FSO2Cl is presented based on the photoactivation electron donor–acceptor (EDA) complex. The reaction avoids requirement for photocatalysts, bases, hydrogen donor reagents, any other additives, and harsh conditions, enabling facile synthesis various functionalized γ-hydroxy (E)-alkenylsulfonyl fluorides. These multifunctional sulfonyl fluorides can be further diversified, providing access to privileged molecules biological relevance.

Language: Английский

Citations

7
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
Unraveling the Potential of Vinyl Ether as an Ethylene Surrogate in Heteroarene C─H Functionalization via the Spin‐Center Shift DOI Creative Commons
Wonjun Choi,

Leejae Kim,

Sungwoo Hong

et al.

Advanced Science, Journal Year: 2024, Volume and Issue: 11(19)

Published: March 13, 2024

Abstract Despite the simplicity and abundance of ethylene, its practical application presents significant hurdles due to nature as a highly flammable gas. Herein, strategic use easily handled vinyl ether is reported latent ethylene surrogate achieved via spin‐center shift (SCS) pathway, enabling successful three‐component reaction that bridges heteroarenes various coupling partners, including sulfinates, thiols, phosphine oxides. Through photoredox catalytic process, α ‐oxy radicals are generated by combining with phenyl ether, which subsequently added N‐heteroarenes. Subsequently, radical‐mediated SCS pathway serves driving force for C─O bond cleavage, effectively engaging phenoxy group leaving group. In addition, broadening utility method, valuable synthon provided efficient C─H vinylation N‐heteroarenes following sulfonyl elimination. This approach not only enriches toolbox synthetic methodology but also provides more streamlined alternative, circumventing challenges associated direct gas usage. The versatility particularly evident in late‐stage functionalizations medicinally relevant molecules peptides, underscores capability produce invaluable compounds vinylated N‐heteroarene derivatives.

Language: Английский

Citations

4
Photoredox-Catalyzed Allylic C–H Fluorosulfonylation of Alkenes: Accessing Allyl Sulfonyl Fluorides DOI

Zhi-Min Yan,

Chunfang Zhang,

Hua Li

et al.

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

Published: Feb. 6, 2025

This study reported a novel and unprecedented photoredox-catalyzed protocol for direct allylic C–H fluorosulfonylation of alkenes with FABI. mild exhibited excellent compatibility various functional groups, broad substrate scope, promising scalability, enabling convenient access to wide range allyl sulfonyl fluorides exceptional regioselectivity. The synthetic robustness this strategy was further demonstrated by the late-stage functionalization natural products their ligation other drugs via SuFEx chemistry.

Language: Английский

Citations

0
Applications of Sulfonyl Fluorides DOI

季虹 俞

Advances in Material Chemistry, Journal Year: 2025, Volume and Issue: 13(02), P. 161 - 170

Published: Jan. 1, 2025

Language: Английский

Citations

0