Copper-Catalyzed Regioselective 1,4-Selenosulfonylation of 1,3-Enynes to Access Cyanoalkylsulfonylated Allenes

Organic Letters, Journal Year: 2021, Volume and Issue: 23(19), P. 7472 - 7476

Published: Sept. 14, 2021

By employing CuOAc as the catalyst, we realize a four-component reaction of 1,3-enynes, diselenides, DABCO·(SO2)2, and cycloketone oxime esters, providing facile access to diverse cyanoalkylsulfonylated allenyl selenides in moderate good yields. This features high functional group tolerance broad substrate scope, enabling regioselective, sequential formation C–SO2 C–Se bonds under mild conditions. Moreover, utility this methodology is further illustrated through late-stage functionalization drug-based molecules.

Language: Английский

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Photoredox-Catalyzed α-Sulfonylation of Ketones from Sulfur Dioxide and Thianthrenium Salts

Organic Letters, Journal Year: 2022, Volume and Issue: 24(15), P. 2955 - 2960

Published: April 13, 2022

A photoredox-catalyzed sulfonylation of silyl enol ethers with DABCO·(SO2)2 and thianthrenium salts is achieved, providing diverse β-keto sulfones in moderate to good yields. This protocol features easily accessible starting materials functional group compatibility, enabling the introduction various functionalized sulfonyl groups into ketones. Furthermore, as one important industrial raw materials, methanol can be employed methyl source prepare α-methylsulfonated ketones through a intermediate for first time.

Language: Английский

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Access to chiral β-sulfonyl carbonyl compounds via photoinduced organocatalytic asymmetric radical sulfonylation with sulfur dioxide

Chemical Science, Journal Year: 2022, Volume and Issue: 13(30), P. 8834 - 8839

Published: Jan. 1, 2022

An organocatalytic enantioselective radical reaction of potassium alkyltrifluoroborates, DABCO·(SO

Language: Английский

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An iron-catalyzed multicomponent reaction of cycloketone oxime esters, alkenes, DABCO·(SO₂)₂ and trimethylsilyl azide

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(4), P. 917 - 922

Published: Jan. 1, 2022

The synthesis of β-azidosulfones starting from alkenes, cycloketone oxime esters, trimethylsilyl azide and a sulfur dioxide surrogate DABCO·(SO 2 ) under iron catalysis is developed.

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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Photoredox-catalyzed reaction of thianthrenium salts, sulfur dioxide and hydrazines

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(14), P. 3781 - 3785

Published: Jan. 1, 2022

A photoredox-catalyzed reaction of thianthrenium salts, hydrazines and DABCO·(SO 2 ) is accomplished, providing diverse arenesulfonohydrazides in moderate to good yields under mild conditions.

Language: Английский

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Construction of sulfonated spiro[5,5]trienones from sulfur dioxide via iron-catalyzed dearomative spirocyclization of biaryls

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(7), P. 1937 - 1942

Published: Jan. 1, 2022

An iron-catalyzed dearomative spirocyclization of biaryl ynones with sodium metabisulfite and cycloketone oxime esters is developed for the construction sulfonated spiro[5,5]trienones.

Language: Английский

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Iminyl radical initiated sulfonylation of alkenes with rongalite under photoredox conditions

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(14), P. 3746 - 3751

Published: Jan. 1, 2021

A photoredox-catalyzed reaction of oximes, rongalite and electrophiles is accomplished, affording pyrrole-substituted aliphatic sulfones or sulfonamides in moderate to good yields.

Language: Английский

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Visible-Light-Mediated Late-Stage Sulfonylation of Boronic Acids via N–S Bond Activation of Sulfonamides

ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(3), P. 1986 - 1991

Published: Jan. 21, 2022

A visible-light-mediated late-stage arylation of N–S bonds in sulfonamides has been developed with using readily available imines as sulfonyl radical source. Diverse complex sulfones could be synthesized by prefunctionalizaiton and subsequent bond arylation, demonstrating the advantages sulfonylation reagents. Additionally, mechanism research revealed that probably both EDA chemistry photoredox catalysis were responsible for formation sulfones. This methodology characterized broad substrate scope simple reaction conditions also high atom economy, since aldehyde synthesis recovered after workup reactions.

Language: Английский

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Photoinduced Alkylsulfonylation and Cyanoalkylsulfonylation of Morita–Baylis–Hillman Adducts via Multicomponent Insertion of Sulfur Dioxide

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(7), P. 4877 - 4887

Published: March 8, 2024

General and convenient visible-light-promoted alkylsulfonylation cyanoalkylsulfonylation of MBH adducts have been developed through the multicomponent insertion sulfur dioxide, enabling assembly two C–S bonds to generate structurally diverse allylic alkylsulfones (43 examples in total). The reaction with potassium alkyltrifluoroborates 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct afforded sulfones generally good yields. Notably, addition N,N,N′,N′-tetramethylethylenediamine as a base into photocatalytic system led yielding an alkyl sulfonyl unit cyano group-anchored trisubstituted alkenes by utilizing cycloketone oxime esters C-radical precursors. Both these reactions constructed bonds, all desired products were obtained moderate excellent yields complete stereospecificity.

Language: Английский

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