Recent advances in the dichalcogenation reactions of unsaturated compounds via double functionalization

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(19), P. 4972 - 5027

Published: Jan. 1, 2023

This review comprehensively summarizes the dichalcogenative functionalization of unsaturated compounds over past decade. The scopes, limitations and detailed reaction mechanisms are also discussed.

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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Photo-induced stereo- and regiospecific sulfonylation of C–C multiple bonds exploiting the dual reactivity of sulfonium iodate(i) species

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(19), P. 4918 - 4926

Published: Jan. 1, 2023

The visible-light-directed stereospecific radical sulfonylation featuring the dual-reactivity of electrophilic reagent Me 3 SI(OAc) 2 is realized for vinyl-sulfonyl functionalization C( sp )-H and π bond in alkynes alkenes.

Language: Английский

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Photochemical aerobic sulfonylation–cyclization–selenylation to indole-fused medium-sized N-heterocycles in 2-Me-THF

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

Published: Jan. 1, 2025

We report a novel visible-light-induced sulfonylation cyclization and aerobic selenylation reaction for the rapid construction of highly functionalized indole-fused medium-sized diazepinones with biomass feedstock 2-Me-THF as medium.

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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Iodine-mediated photoinduced tuneable disulfonylation and sulfinylsulfonylation of alkynes with sodium arylsulfinates

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(50), P. 7767 - 7770

Published: Jan. 1, 2023

The iodine-mediated reaction of alkynes with sodium arylsulfinates under blue light irradiation gives either disulfonylation or sulfinylsulfonation depending on conditions.

Language: Английский

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Green and rapid acid-catalyzed ynamide skeletal rearrangement and stereospecific functionalization with anisole derivatives

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(20), P. 8124 - 8133

Published: Jan. 1, 2023

Environmentally friendly acid-catalyzed 2-alkynyl-ynamides (N–Csp) bond cleavage, alkyne migration and stereospecific functionalization with anisole derivatives for the synthesis of challenging indole scaffolds in 5–10 minutes.

Language: Английский

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Radical relay strategy for the construction of alkylsulfonated indolo[2,1-a]isoquinoline-6(5H)-ones via SO₂ insertion/Smiles rearrangement

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

A new radical relay approach for the efficient construction of alkylsulfonated indolo[2,1- a ]isoquinoline-6(5 H )-ones in moderate to good yields under mild conditions via SO 2 insertion/Smiles rearrangement/intramolecular cyclization is developed.

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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Recent Developments in C‐S, C‐Se Bond Formation via Three‐Component Reactions of Alkynes

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(46)

Published: Aug. 28, 2024

Abstract Alkynes are valuable building blocks in organic synthesis. They can undergo three‐component difunctionalization to create sulfur or selenium‐containing compounds. Three‐component reactions of alkynes atom economic, practical and regioselective. This review will disscuss decade developments, including C−S C−Se bond formation via thiolation, sulfonylation selenylation. Recent developments be mainly categorized into three types. (1) Radical C−S/S−Se is a hot topic. Reactions initiated by S/Se radicals other exhibit two types selectivities. Photochemical electrochemical under eco‐friendly conditions have been increasingly reported. (2) Some transformations involve electrophilic three‐membered ring intermediates. Thiiraniums, seleniraniums, iodoniums among the most prevalent species. ring‐opening various nucleophiles participate tandem reactions. (3) Metal‐catalyzed reactions, classic category, also discussed text. In following section, we provide an overview based on mechanisms substrates. The roles added reagents discussed.

Language: Английский

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