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.

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.

scholarly journals Metal-free selective mono-halodecarboxylation of heteroarenes under mild conditions

2018 ◽  
Vol 5 (6) ◽  
pp. 180333 ◽  
Author(s):  
Scott H. Henderson ◽  
Ryan A. West ◽  
Simon E. Ward ◽  
Mark A. Honey
Keyword(s):  
Carboxylic Acids ◽  
Toxic Metal ◽  
Metal Catalysts ◽  
Metal Free ◽  
Mild Conditions ◽  
Simple Protocol ◽  
Convenient Route

The halodecarboxylation of heteroarene carboxylic acids by treatment with N -bromosuccinimide or N -chlorosuccinimide was performed. This procedure provides a convenient route to synthetically useful mono-halogenated heteroarene intermediates such as halo-indoles, -aza-indoles, -indazoles and -aza-indazoles. The mild conditions employed and simple protocol provides an advantage over traditional halodecarboxylation procedures that require expensive and toxic metal catalysts, basic conditions, time-consuming intermediate isolation and elevated reaction temperatures.

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.

Metal-free insertion of sulfur dioxide with aryl iodides under ultraviolet irradiation: direct access to sulfonated cyclic compounds

2020 ◽  
Vol 7 (1) ◽  
pp. 14-18 ◽  
Author(s):  
Shengqing Ye ◽  
Kaida Zhou ◽  
Pornchai Rojsitthisak ◽  
Jie Wu
Keyword(s):  
Sulfur Dioxide ◽  
Ultraviolet Irradiation ◽  
Room Temperature ◽  
Direct Access ◽  
Metal Free ◽  
Mild Conditions ◽  
Aryl Iodides ◽  
Convenient Route ◽  
Cyclic Compounds ◽  
Allylic Bromide

Metal-free insertion of sulfur dioxide with aryl iodides and silyl enolates or allylic bromide under ultraviolet irradiation at room temperature is accomplished. This protocol provides a convenient route to sulfonated cyclic compounds under mild conditions.

Schiff-base molecules and COFs as metal-free catalysts or silver supports for carboxylation of alkynes with CO2

2021 ◽  
Author(s):  
Lin Zhang ◽  
Ran Bu ◽  
Xiao-yan Liu ◽  
Peng-fei Mu ◽  
En-Qing Gao
Keyword(s):  
Schiff Base ◽  
Transition Metal ◽  
Co2 Fixation ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Terminal Alkynes ◽  
Metal Free ◽  
Mild Conditions

Carboxylating terminal alkynes with CO2 to produce propiolic acids is an atom-economic and high-value route for CO2 fixation and utilization, but the conversion under mild conditions needs transition metal catalysts....

Transition-metal-free direct perfluoroalkylation of quinoline amides at C5 position through radical cross-coupling under mild conditions

2017 ◽  
Vol 4 (6) ◽  
pp. 1116-1120 ◽  
Author(s):  
Jun Xu ◽  
Li Qiao ◽  
Beibei Ying ◽  
Xiaolei Zhu ◽  
Chao Shen ◽  
...  
Keyword(s):  
Transition Metal ◽  
Efficient Method ◽  
Cross Coupling ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Low Energy ◽  
Metal Free ◽  
Mild Conditions

A simple low-energy and efficient method is established for the synthesis of C5-selective perfluoroalkylation quinolines in the absence of any transition metal catalysts.

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...

scholarly journals One Pot and Metal-Free Approach to 3-(2-Hydroxybenzoyl)-1-aza-anthraquinones

Molecules ◽  
2019 ◽  
Vol 24 (16) ◽  
pp. 3017
Author(s):  
Jiaqi Yuan ◽  
Qian He ◽  
Shanshan Song ◽  
Xiaofei Zhang ◽  
Zehong Miao ◽  
...  
Keyword(s):  
Transition Metal ◽  
Functional Group ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Inert Gas ◽  
One Pot ◽  
Metal Free ◽  
Mild Conditions ◽  
Anthraquinone Derivatives

Herein, a direct strategy to synthesize 3-(2-hydroxybenzoyl)-1-aza-anthraquinones with excellent efficiency, mild conditions, and benign functional group compatibility was reported. A variety of 3-formylchromone compounds were employed as compatible substrates and this protocol gave the 3-(2-hydroxybenzoyl)-1-aza-anthraquinone derivatives in good to excellent yields without inert gas and expensive transition metal catalysts. Some compounds displayed good anti-proliferative activities.

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.

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