Recent advancements in metal‐catalyst‐free multicomponent radical sulfonylation of alkynes

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(43)

Published: June 4, 2024

Vinyl sulfones are crucial building blocks in synthetic chemistry and core structural units of pharmaceutically active molecules, thus extensive investigations have been conducted on the construction these skeletons. In contrast to classical approaches, radical sulfonylation alkynes for producing vinyl has garnered considerable interest because its mild conditions high efficiency. Radical sulfonation typically begins with sulfonyl attacking alkynes, followed by further functionalization. Moreover, association metal-catalyst-free systems multicomponent reactions (MCRs) offers an environmentally friendly pathway efficiently constructing complex scaffolds from readily available partners. However, there is no comprehensive review summarizing advancements alkynes. Hence, we provide a categorical overview based objects (hydrosulfonylation, carbosulfonylation, aminosulfonylation, oxysulfonylation, sulfosulfonylation, selenosulfonylation, iodosulfonylation), along interpretations reaction mechanisms.

Language: Английский

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Electrochemical Sulfonylation/Cyclization of N-Alkenylacrylamides with Sodium Sulfinates or Sulfonyl Hydrazides

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10660 - 10677

Published: July 18, 2024

Two general protocols for the regioselective electrochemically enabled sulfonylation cyclization of

Language: Английский

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Recent trends in the synthesis and applications of β-iodovinyl sulfones: a decade of progress

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(13), P. 2492 - 2509

Published: Jan. 1, 2024

Over the past decade, there has been exponential growth in vicinal iodosulfonylation of alkynes using sulfonyl and iodide reactants. This review highlights recent developments β-iodovinyl sulfones their applications organic synthesis.

Language: Английский

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Radical-mediated sulfonylation relay of alkyl alkynes/alkenes and electron-deficient alkenes to access vinyl and alkyl sulfones

Organic Chemistry Frontiers, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A radical-mediated sulfonylation relay of alkyl alkynes/alkenes with electron-deficient alkenes using Na 2 S O 4 as a linker is developed to synthesize highly selective ( Z )-vinyl and sulfones under metal-free catalyzed system.

Language: Английский

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Metal-free iodosulfonylation of alkynes to access (E)-β-iodovinyl sulfones in water

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

We report a metal-free iodosulfonylation of alkynes in water at room temperature, which efficiently produces ( E )-β-iodovinyl sulfones good to excellent yields with high regio- and stereoselectivity.

Language: Английский

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Synthesis of (E)‐β‐Iodovinyl Sulfones via HI‐mediated Vicinal Iodosulfonylation of Alkynes with Sodium Sulfinates

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 13(6)

Published: March 21, 2024

Abstract Hydroiodic acid‐mediated vicinal iodosulfonylation reaction of alkynes with sodium sulfinates is proposed for the synthesis ( E )‐ β ‐iodovinyl sulfones. The method easy to operate, environmentally friendly, using inexpensive and easily available raw materials, giving target products good regio‐ stereoselectivity in satisfactory yields.

Language: Английский

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Photocatalytic iodosulfonylation of internal alkynes under green conditions

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(8), P. 4653 - 4658

Published: Jan. 1, 2024

Photocatalytic iodosulfonylation in ethanol allows the isolation of β-iodovinyl aryl and alkyl sulfones after dilution reaction mixture with water filtration.

Language: Английский

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Visible-Light-Mediated Dual Functionalization of Allenes: Regio- and Stereoselective Synthesis of Vinylsulfone Azides

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 89(1), P. 665 - 675

Published: Dec. 20, 2023

A gentle and effective method for the photocatalytic dual functionalization of allenes with high regio- stereoselectivity using a nonmetallic catalyst is described. Inexpensive easily available sulfinates TMSN3 were employed as sulfone azido sources, respectively. The characterized by satisfactory substrate compatibility tolerance toward functional groups. straightforward initial mechanistic experiments suggested that reaction could follow radical pathway. synthesis vinylsulfone azide derivatives presented here offers promising scaffold future development vinyl sulfone-based drugs bioorthogonal reagents.

Language: Английский

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Photoinitiated by Red Light (λ 625 nm) Iodosulfonylation of Internal Alkynes to Synthesize β-Iodovinyl Sulfones

Russian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 59(12), P. 2102 - 2106

Published: Dec. 1, 2023

Abstract A number of β-iodovinyl sulfones were synthesized by direct difunctionalization internal alkynes with arenesulfonyl iodides under irradiation red light (λ max 625 nm) generated an economical LED source. The products obtained in high yields (68–99%) from equimolar amounts the reactants. reaction sulfonyl follows a radical mechanism and provides regioselective method synthesis sulfones.

Language: Английский

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Photoinitiated by red light (625 nm) iodosulfonylation of internal alkynes to synthesize β-iodovinylsulfones

Журнал органической химии, Journal Year: 2023, Volume and Issue: 59(12), P. 1620 - 1625

Published: Dec. 15, 2023

Language: Английский

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