Copper-catalyzed three-component reaction of arylhydrazine hydrochloride, DABSO, and NFSI for the synthesis of arenesulfonyl fluoride

2021 ◽  
Author(s):  
Qijun Pan ◽  
Yongan Liu ◽  
Wan Pang ◽  
Jingjing Wu ◽  
Xiaoyu Ma ◽  
...  
Keyword(s):  
Sulfur Dioxide ◽  
Good Yield ◽  
Mild Conditions ◽  
Three Component Reaction

This paper reports a convevient copper-catalyzed three-component conversion of arylhydrazine hydrochloride to arenesulfonyl fluoride in good yield under mild conditions, using 1,4-diazabicyclo [2.2.2]octane bis(sulfur dioxide) (DABSO) as the sulfonyl source...

C–H bond sulfonylation of anilines with the insertion of sulfur dioxide under metal-free conditions

2018 ◽  
Vol 54 (54) ◽  
pp. 7459-7462 ◽  
Author(s):  
Kaida Zhou ◽  
Jun Zhang ◽  
Lifang Lai ◽  
Jiang Cheng ◽  
Jiangtao Sun ◽  
...  
Keyword(s):  
Sulfur Dioxide ◽  
Metal Catalysts ◽  
Metal Free ◽  
Mild Conditions ◽  
Three Component Reaction

2-Sulfonylanilines are generated in moderate to good yields through a three-component reaction of anilines, DABCO·(SO2)2, and aryldiazonium tetrafluoroborates under mild conditions. No metal catalysts or additives are needed for this transformation.

A Facile and Diastereoselective access to Functionalised Benzopyrano[3,4-a] Quinolizines via a Pyridine-Based Three-Component Reaction

2017 ◽  
Vol 41 (12) ◽  
pp. 688-692
Author(s):  
Abbas Ali Esmaeili ◽  
Abbas Moradi ◽  
Mahdieh Zangouei ◽  
Ali Reza Fakhari ◽  
Tooba Tabibi
Keyword(s):  
Good Yield ◽  
Condensation Reaction ◽  
Mild Conditions ◽  
Dialkyl Acetylenedicarboxylates ◽  
Three Component Reaction

The reaction of 2-oxo-2 H-chromene-3-carbonitriles with dialkyl acetylenedicarboxylates and pyridines results in a three-component condensation reaction in which the 2-oxo-2 H-chromene-3-carbonitrile group acts as a dipolarophile to produce benzopyrano[3,4- a] quinolizines under mild conditions in good yield.

Photoredox-catalyzed sulfonylation of difluoroenoxysilanes with the insertion of sulfur dioxide

2020 ◽  
Vol 56 (66) ◽  
pp. 9469-9472 ◽  
Author(s):  
Fu-Sheng He ◽  
Yanfang Yao ◽  
Wenlin Xie ◽  
Jie Wu
Keyword(s):  
Sulfur Dioxide ◽  
Sodium Metabisulfite ◽  
Silyl Ethers ◽  
Mild Conditions ◽  
Three Component Reaction ◽  
Enol Silyl Ethers

A photoredox-catalyzed three-component reaction of aryldiazonium tetrafluoroborates with sodium metabisulfite and 2,2-difluoro enol silyl ethers is described, providing α,α-difluoro-β-ketosulfones in moderate to good yields under mild conditions.

Photoinduced synthesis of (E)-vinyl sulfones through the insertion of sulfur dioxide

2018 ◽  
Vol 5 (21) ◽  
pp. 3153-3157 ◽  
Author(s):  
Tong Liu ◽  
Yechun Ding ◽  
Xiaona Fan ◽  
Jie Wu
Keyword(s):  
Sulfur Dioxide ◽  
Visible Light ◽  
Visible Light Irradiation ◽  
Light Irradiation ◽  
Mild Conditions ◽  
Three Component Reaction ◽  
Photoinduced Synthesis

Under visible light irradiation, a three-component reaction of potassium alkyltrifluoroborates, sulfur dioxide and alkynes with the assistance of photocatalysis and in the presence of copper(ii) triflate is described. This transformation affords (E)-vinyl sulfones efficiently with excellent regioselectivity and stereoselectivity under mild conditions.

Thiosulfonylation of alkenes with the insertion of sulfur dioxide under non-metallic conditions

2018 ◽  
Vol 5 (20) ◽  
pp. 2940-2944 ◽  
Author(s):  
Fu-Sheng He ◽  
Youqian Wu ◽  
Jun Zhang ◽  
Hongguang Xia ◽  
Jie Wu
Keyword(s):  
Sulfur Dioxide ◽  
High Efficiency ◽  
Mild Conditions ◽  
Three Component Reaction

A three-component reaction of 1-(2-allylaryl)thioureas, sulfur dioxide, and aryldiazonium tetrafluoroborates under mild conditions is realized, leading to sulfonated [3,1]-benzothiazepines in good yields. High efficiency is observed for this non-metallic transformation.

Generation of N-aminosulfonamides via a photo-induced fixation of sulfur dioxide into aryl/alkyl halides

2016 ◽  
Vol 3 (5) ◽  
pp. 574-578 ◽  
Author(s):  
Yuewen Li ◽  
Danqing Zheng ◽  
Zhenhua Li ◽  
Jie Wu
Keyword(s):  
Sulfur Dioxide ◽  
Ultraviolet Irradiation ◽  
Alkyl Halides ◽  
Mild Conditions ◽  
Catalyst Free ◽  
Redox Catalysts ◽  
Three Component Reaction

A catalyst-free aminosulfonylation through insertion of sulfur dioxide with aryl/alkyl halides enabled by photoenergy is presented. Under ultraviolet irradiation, a three-component reaction of aryl/alkyl halides, sulfur dioxide, and hydrazines proceeds under mild conditions without any metals or photo-redox catalysts.

Generation of (E)-β-sulfonyl enamines from sulfur dioxide via a radical process

2021 ◽  
Vol 8 (8) ◽  
pp. 1789-1794
Author(s):  
Xiaodong Tu ◽  
Jiapian Huang ◽  
Wenlin Xie ◽  
Tonghao Zhu ◽  
Jie Wu
Keyword(s):  
Sulfur Dioxide ◽  
Radical Process ◽  
Three Component Reaction

An iron(ii)-catalyzed three-component reaction of O-acyl oximes, sulfur dioxide, and N-vinylacetamides is accomplished. Diverse (E)-β-sulfonyl enamines are obtained in moderate to good yields by using this protocol with excellent stereoselectivity and regioselectivity.

Synthesis of 6-(sulfonylmethyl)phenanthridines through a reaction of aryldiazonium tetrafluoroborates, sulfur dioxide, and vinyl azides

2018 ◽  
Vol 5 (17) ◽  
pp. 2555-2559 ◽  
Author(s):  
Xuefeng Wang ◽  
Yuewen Li ◽  
Guanyinsheng Qiu ◽  
Jie Wu
Keyword(s):  
Sulfur Dioxide ◽  
Three Component Reaction ◽  
Vinyl Azides

Synthesis of 6-(sulfonylmethyl)phenanthridines through a three-component reaction of aryldiazonium tetrafluoroborates, a sulfur dioxide surrogate of DABCO·(SO2)2, and vinyl azides under metal- and additive-free conditions is achieved.

Consecutive Multicomponent Reactions: Synthesis of 3-Acyl-4-alkynyl-Substituted 1,3-Thiazolidines

Synthesis ◽  
2018 ◽  
Vol 50 (05) ◽  
pp. 1123-1132 ◽  
Author(s):  
Jürgen Martens ◽  
Torben Schlüter ◽  
Nils Frerichs ◽  
Marc Schmidtmann
Keyword(s):  
Functional Groups ◽  
Multicomponent Reactions ◽  
Terminal Alkynes ◽  
Synthetic Route ◽  
Acyl Chlorides ◽  
Mild Conditions ◽  
Three Component Reaction

This work describes the synthesis of compounds containing thiazolidine and propargylamidic motifs. Their preparation follows a synthetic route containing two multicomponent reactions. First, the Asinger four-component reaction is used to prepare 3-thiazolines and 3-oxazolines. Secondly, these heterocyclic imines are converted into propargylamides by a copper-catalyzed three-component reaction using acyl chlorides and terminal alkynes. The synthetic route is characterized by mild conditions and many functional groups are tolerated. The formation of an unexpected α-alkynoxyamide is also presented.

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