Magnetically recoverable catalysts for efficient multicomponent synthesis of organosulfur compounds

RSC Advances, Journal Year: 2025, Volume and Issue: 15(5), P. 3928 - 3953

Published: Jan. 1, 2025

This review studies magnetically recoverable catalysts designed for the efficient multicomponent synthesis of organosulfur compounds. These enhance process by combining efficiency with environmental sustainability.

Language: Английский

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Accessing chiral sulfones bearing quaternary carbon stereocenters via photoinduced radical sulfur dioxide insertion and Truce–Smiles rearrangement

Nature Communications, Journal Year: 2022, Volume and Issue: 13(1)

Published: Nov. 18, 2022

Abstract From the viewpoint of synthetic accessibility and functional group compatibility, photoredox-catalyzed sulfur dioxide insertion strategy enables in situ generation functionalized sulfonyl radicals from easily accessible starting materials under mild conditions, thereby conferring broader application potential. Here we present two complementary photoinduced systems to trigger radical asymmetric Truce–Smiles rearrangements for preparing a variety chiral sulfones that bear quaternary carbon stereocenter. This protocol features broad substrate scope excellent stereospecificity. Aside scalability, introduction stereocenter at position β bioactive molecule-derived further demonstrates practicality potential this methodology.

Language: Английский

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Asymmetric sulfonylation with sulfur dioxide surrogates: a new access to enantiomerically enriched sulfones

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(26), P. 3821 - 3826

Published: Jan. 1, 2023

In this highlight, we survey recent exciting advances in asymmetric sulfonylation by using sulfur dioxide surrogates, and discuss induction modes, reaction mechanisms, substrate scope opportunities for further studies.

Language: Английский

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Copper‐Catalyzed Remote Enantioselective Sulfonylation of Yne‐Allylic Esters with Sodium Sulfinates

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(52)

Published: Nov. 13, 2023

Impressive progress has been made in the copper-catalyzed asymmetric propargylic substitution (APS) reaction, but its use remote yne-allylic remains a challenging topic. Herein, we report first enantioselective sulfonylation of esters with sodium sulfinates. The reaction is assumed to occur via copper-vinylvinylidene species as key reactive intermediate. readily available starting materials, mild conditions, and excellent regio-, enantio- stereoselectivity, well broad substrate scope (>70 examples), show practicality attractiveness this method.

Language: Английский

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A general copper-catalysed enantioconvergent C(sp3)–S cross-coupling via biomimetic radical homolytic substitution

Nature Chemistry, Journal Year: 2023, Volume and Issue: 16(3), P. 466 - 475

Published: Dec. 6, 2023

Language: Английский

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Carbene-Catalyzed Enantioselective Sulfonylation of Enone Aryl Aldehydes: A New Mode of Breslow Intermediate Oxidation

Journal of the American Chemical Society, Journal Year: 2022, Volume and Issue: 144(12), P. 5441 - 5449

Published: March 11, 2022

A carbene-catalyzed sulfonylation reaction between enone aryl aldehydes and sulfonyl chlorides is disclosed. The effectively installs sulfone moieties in a highly enantioselective manner to afford sulfone-containing bicyclic lactones. chloride behaves both as an oxidant nucleophilic substrate (via its reduced form) this N-heterocyclic carbene (NHC)-catalyzed process. NHC catalyst provides activation stereoselectivity control on very remote site of aldehyde substrates. Water plays important role modulating deactivation reactivation routes that involve reactions chloride. Experimental studies DFT calculations suggest unprecedented intermediate new oxidation mode the NHC-derived Breslow are involved asymmetric reaction.

Language: Английский

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Progress in the Electrochemical Reactions of Sulfonyl Compounds

ChemSusChem, Journal Year: 2022, Volume and Issue: 15(7)

Published: Feb. 17, 2022

Abstract Electrosynthesis has recently attracted more and attention due to its great potential replace chemical oxidants or reductants in molecule‐electrode electron transfer. Sulfonyl compounds such as sulfonyl hydrazides, sulfinic acids (and their salts), halides have been discovered practical precursors of several radicals. As electrochemical redox reactions can provide green efficient pathways for the activation compounds, studies electrosynthesis rapidly increased. Several types radicals be generated from anodic oxidation cathodic reduction initiate fluoroalkylation, benzenesulfonylation, cyclization rearrangement. In this Review, we summarize developments involving mainly last decade.

Language: Английский

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Enantioselective Synthesis of Allylic Sulfones via Rhodium-Catalyzed Direct Hydrosulfonylation of Allenes and Alkynes

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(25), P. 16996 - 17002

Published: June 14, 2024

A highly regio- and enantioselective hydrosulfonylation using commercially available sodium sulfinates is reported, providing the first direct asymmetric rhodium-catalyzed of allenes/alkynes to synthesize chiral allylic sulfones. Ligand screening studies demonstrated indispensable role C1-symmetric P,N-ligand (Rax,S,S)-StackPhim for achieving both high regioselecitivity (>20:1) enantioselectivity (up 97% ee). Notably, operationally simple method mild conditions allow rapid preparation sulfones with a wide scope functional groups. Moreover, use tert-butyldimethylsilyloxymethanesulfinate enables collective synthesis various sulfone derivatives after transformations protected hydroxymethyl product.

Language: Английский

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Regiodivergent and Enantioselective Synthesis of Cyclic Sulfones via Ligand‐Controlled Nickel‐Catalyzed Hydroalkylation

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(29)

Published: April 29, 2024

Abstract Cyclic sulfones have demonstrated important applications in drug discovery. However, the catalytic and enantioselective synthesis of chiral cyclic remains challenging. Herein, we develop nickel‐catalyzed regiodivergent hydroalkylation sulfolenes to streamline alkyl sulfones. The method has broad scope high functional group tolerance. regioselectivity can be controlled by ligands only. A neutral PYROX ligand favors C3‐alkylation whereas an anionic BOX C2‐alkylation. This control is kinetic origin as C2‐bound Ni intermediates are always thermodynamically more stable. Reactivity study a wide range relevant reveal I /Ni III cycle with II −H species resting state. regio‐ enantio‐determining step insertion this into 2‐sulfolene. work provides efficient for class organic compounds enhances mechanistic understanding Ni‐catalyzed stereoselective hydroalkylation.

Language: Английский

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Synthesis of I(III)/S(VI) reagents and their reactivity in photochemical cycloaddition reactions with unsaturated bonds

Nature Communications, Journal Year: 2022, Volume and Issue: 13(1)

Published: Nov. 3, 2022

The development of novel methodologies for the introduction sulfoxonium group under mild conditions is appealing but remains underexplored. Herein we report synthesis a class hypervalent iodine reagents with transferrable group. These compounds enable mixed iodonium-sulfoxonium ylide reactivity. well-defined are examined in visible-light-promoted cyclization reactions wide range unsaturated bonds including alkenes, alkynes, nitriles, and allenes. Two distinct pathways identified, which controlled by substituent bond. cycloaddition protocol features simple operation, reaction conditions, excellent functional tolerance, affording broad sulfoxonium-containing cyclic structures moderate to yields. Furthermore, sufoxonium product can be transformed into diverse groups structural motifs via single electron transfer transition-metal catalysis.

Language: Английский

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