FSO2 Radical-Initiated Photoredox Cyclization of 4-Enoic Acids to Functionalized γ-Lactones DOI
Saihu Liao, Xin Fang,

Xuebing Geng

et al.

Synthesis, Journal Year: 2023, Volume and Issue: 56(11), P. 1727 - 1734

Published: Dec. 19, 2023

Abstract The incorporation of sulfonyl fluoride groups into molecules has been proven effective in enhancing their biological activities or introducing new functions. Herein, a transition-metal-free and visible-light-mediated radical tandem cyclization unsaturated carboxylic acid is reported. This affords facile access to FSO2-functionalized γ-lactones efficiently, which are critical structural motifs widely present biologically active molecules.

Language: Английский

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
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
Synthetic strategies for fluorosulfonylated compounds: application to click chemistry reactions DOI
Sebastián Barata‐Vallejo, Damian E. Yerien, Al Postigo

et al.

Catalysis Science & Technology, Journal Year: 2023, Volume and Issue: 13(9), P. 2597 - 2617

Published: Jan. 1, 2023

Fluorosulfonylation of (hetero)aromatic and aliphatic compounds with emphasis on the use fluorosulfonylating hubs is discussed. Examples click chemistry (SuFEx) reactions diversity oriented clicking (DOC) processes are provided.

Language: Английский

Citations

18
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
Fluorosulfonyl Arylation of Alkynes via Electron Donor–Acceptor Photoactivation DOI

Haoyuan Cheng,

Tianyu He, Dengfeng Chen

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(17), P. 3581 - 3585

Published: April 25, 2024

A radical fluorosulfonyl arylation of alkynes with sulfuryl chlorofluoride as the FSO2 precursor via electron donor–acceptor photoactivation driven by daylight or a blue light-emitting diode is disclosed. series valuable benzo-fused carbocycles and heterocycles have been produced simple operation under mild conditions in absence any external catalysts additives. The synthetic potential this protocol has further demonstrated excellent scalability, well diverse postderivatizations, including SuFEx reactions other useful cascade reactions.

Language: Английский

Citations

5
Nitrogen-Based Organofluorine Functional Molecules: Synthesis and Applications DOI
Shuai Liu, Jun Zhou, Lu Yu

et al.

Chemical Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: April 22, 2025

Fluorine and nitrogen form a successful partnership in organic synthesis, medicinal chemistry, material sciences. Although fluorine-nitrogen chemistry has long rich history, this field received increasing interest made remarkable progress over the past two decades, driven by recent advancements transition metal organocatalysis photochemistry. This review, emphasizing contributions from 2015 to 2023, aims update state of art synthesis applications nitrogen-based organofluorine functional molecules chemistry. In dedicated sections, we first focus on fluorine-containing reagents organized according type groups attached nitrogen, including N-F, N-RF, N-SRF, N-ORF. review also covers nitrogen-linked building blocks, catalysts, pharmaceuticals, agrochemicals, underlining these components' broad applicability growing importance modern

Language: Английский

Citations

0
Synthesis of 3-sulfonylisoindolin-1-ones from olefinic amides and sodium sulfinates via electrooxidative tandem cyclization DOI

X. X. Wang,

Ziyue Zhao, Jiajie Guo

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(29), P. 5897 - 5901

Published: Jan. 1, 2024

Sulfonyl groups are motifs that widely found in biologically active compounds and drug molecules, many isolated natural products as well pharmaceuticals contain sulfonyl groups. Herein, we present the synthesis of sulfonyl-substituted isoindolones by a electrochemical oxidative radical cascade cycloaddition reaction olefinic amides with sodium sulfite under oxidant- catalyst-free conditions. Various sulfinates were compatible gave desired yields up to 99%.

Language: Английский

Citations

3
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

Citations

6
Photoreduction of Anthracenes Catalyzed by peri‐Xanthenoxanthene: a Scalable and Sustainable Birch‐Type Alternative DOI Creative Commons
C. Luca, Davide Zanetti, Tommaso Battisti

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(63)

Published: Aug. 19, 2023

The typical Birch reduction transforms arenes into cyclohexa-1,4-dienes by using alkali metals, an alcohol as a proton source, and amine solvent. Capitalizing on the strong photoreductive properties of peri-xanthenoxanthene (PXX), herein we report photocatalyzed "Birch-type" acenes employing visible blue light irradiation at room temperature in presence air. Upon excitation 405 or 460 nm mixture N,N-diisopropylethylamine (DIPEA) trifluoromethanesulfonimide (HNTf2 ) DMSO, PXX photocatalyzes selective full-carbon acene derivatives (24-75 %). Immobilization onto polydimethylsiloxane (PDMS) beads (PXX-PDMS) allowed use catalyst heterogeneous batch reactions, giving 9-phenyl-9,10-dihydroanthracene high yield (68 could easily be recovered reused, with no notable drop performance observed after five reaction cycles. Integration PXX-PDMS microreactor enabled under continuous-flow conditions, thereby validating sustainability scalability this heterogeneous-phase approach.

Language: Английский

Citations

4