Recent advances in photochemical and electrochemical strategies for the synthesis of sulfonyl fluorides

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

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Metal-free photosensitized aminosulfonylation of alkenes: a practical approach to β-amido sulfones

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(10), P. 3857 - 3863

Published: Jan. 1, 2023

A general and environmentally friendly organic photo-induced strategy was developed for the synthesis of diverse alkyl-substituted β-amino sulfone derivatives, including primary, secondary, tertiary products.

Language: Английский

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Synthetic strategies for fluorosulfonylated compounds: application to click chemistry reactions

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

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Photocatalytic C–C Bond Cleavage and Fluorosulfonylation of Strained Cycloalkanols for Carbonyl-Containing Aliphatic Sulfonyl Fluorides

Organic Letters, Journal Year: 2023, Volume and Issue: 25(38), P. 7051 - 7056

Published: Sept. 20, 2023

In this report, we present a photocatalytic ring-opening fluorosulfonylation of strained cycloalkanols with sulfur dioxide and NFSI under mild conditions for the synthesis carbonyl-containing aliphatic sulfonyl fluorides. The synthetic potential fluoride products has been examined by diverse transformations, including SuFEx reactions Baeyer-Villiger oxidation reactions. Mechanistic studies demonstrate that reaction operates through radical C-C bond cleavage/SO2 insertion/fluorination cascade process.

Language: Английский

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Copper-catalyzed direct decarboxylative fluorosulfonylation of aliphatic carboxylic acids

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(67), P. 9409 - 9412

Published: Jan. 1, 2022

Sulfonyl fluorides are emerging as key structural motifs in organic synthesis, medicinal chemistry, and materials science. Herein we report two efficient complementary methods for direct decarboxylative fluorosulfonylation of carboxylic acids by the merging copper catalysis with different N-centered HAT regents. A wide range structurally diverse sulfonyl was readily accessed from primary, secondary, tertiary a single step under mild conditions.

Language: Английский

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

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

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Switchable carbo-fluorosulfonylation and hydro-fluorosulfonylation of alkenes enabled by bifunctional fluorosulfonyl radical precursors

Chem Catalysis, Journal Year: 2023, Volume and Issue: 3(12), P. 100821 - 100821

Published: Nov. 28, 2023

Language: Английский

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

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

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Photoredox-catalyzed intermolecular azidosulfonylation of alkenes with DABCO·(SO₂)₂, trimethylsilyl azide and thianthrenium salts

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 10(4), P. 866 - 871

Published: Dec. 21, 2022

Synthesis of β-azido alkylsulfones through a photoredox-catalyzed azido sulfonylation alkenes with DABCO·(SO 2 ) , trimethylsilyl azide and alkyl thianthrenium salts is developed.

Language: Английский

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Radical Fluorosulfonyl Arylation of Alkenes: Accessing FSO₂-Functionalized Chromanes via Formal Endo and Exo Cyclization

Organic Letters, Journal Year: 2022, Volume and Issue: 24(44), P. 8170 - 8175

Published: Oct. 31, 2022

The introduction of sulfonyl fluoride groups into bioactive molecules can often bring about enhanced biological activity, which has attracted more research interest in chemical biology and drug development recent years. Here, we report the a radical fluorosulfonylation alkenes/intramolecular arylation cascade for construction chromanes with attached. 1,2-fluorosulfonyl reactions proceed well both endo exo cyclization fashions, allowing further variation distance between chromane core group.

Language: Английский

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