An unexpected reaction of aryldiazonium tetrafluoroborates, sodium metabisulfite, and thiourea under photoinduced conditions

2019 ◽  
Vol 6 (11) ◽  
pp. 1863-1867 ◽  
Author(s):  
Xinxing Gong ◽  
Xiaofang Li ◽  
Wenlin Xie ◽  
Jie Wu ◽  
Shengqing Ye
Keyword(s):  
Sodium Metabisulfite ◽  
Radical Coupling ◽  
Three Component Reaction ◽  
Unexpected Reaction ◽  
Photoinduced Synthesis

A photoinduced synthesis of S-aryl thiosulfonates through a three-component reaction of aryldiazonium tetrafluoroborates, sodium metabisulfite, and thiourea is achieved. In this transformation, a radical coupling pathway is proposed.

Transition-metal- and oxidant-free three-component reaction of quinoline N-oxides, sodium metabisulfite and aryldiazonium tetrafluoroborates via a dual radical coupling process

2019 ◽  
Vol 17 (43) ◽  
pp. 9479-9488 ◽  
Author(s):  
Guirong You ◽  
Dan Xi ◽  
Jian Sun ◽  
Liqiang Hao ◽  
Chengcai Xia
Keyword(s):  
Transition Metal ◽  
Sodium Metabisulfite ◽  
Coupling Process ◽  
Radical Coupling ◽  
Three Component Reaction

Synthesis of 2-sulfonylquinolines via a three-component reaction of quinoline N-oxides, sodium metabisulfite, and aryldiazonium tetrafluoroborates under transition-metal- and oxidant-free conditions.

Benzylic C(sp3)–H bond sulfonylation of 4-methylphenols with the insertion of sulfur dioxide under photocatalysis

2018 ◽  
Vol 54 (79) ◽  
pp. 11172-11175 ◽  
Author(s):  
Xinxing Gong ◽  
Jiahao Chen ◽  
Lifang Lai ◽  
Jiang Cheng ◽  
Jiangtao Sun ◽  
...  
Keyword(s):  
Sulfur Dioxide ◽  
Sodium Metabisulfite ◽  
Three Component Reaction

Sulfonylation of the benzylic C–H bond is developed through a three-component reaction of aryldiazonium tetrafluoroborates, 4-methylphenols and sodium metabisulfite (Na2S2O5). The inorganic sulfite of sodium metabisulfite is used as the SO2 surrogate.

New Three-Component Reaction:  Novel Formation of a Seven-Membered Ring by the Unexpected Reaction at the γ-Position of the β-Keto Ester

2007 ◽  
Vol 9 (9) ◽  
pp. 1687-1690 ◽  
Author(s):  
Hiromichi Fujioka ◽  
Kenichi Murai ◽  
Ozora Kubo ◽  
Yusuke Ohba ◽  
Yasuyuki Kita
Keyword(s):  
Membered Ring ◽  
Keto Ester ◽  
Three Component Reaction ◽  
Unexpected Reaction

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 allylic sulfones using potassium metabisulfite as the source of sulfur dioxide

2019 ◽  
Vol 6 (1) ◽  
pp. 36-40 ◽  
Author(s):  
Jun Zhang ◽  
Kaida Zhou ◽  
Guanyinsheng Qiu ◽  
Jie Wu
Keyword(s):  
Sulfur Dioxide ◽  
Ultraviolet Irradiation ◽  
Room Temperature ◽  
Alkyl Halides ◽  
Three Component Reaction ◽  
Photoinduced Synthesis

Synthesis of allylic sulfones through a photoinduced three-component reaction of aryl/alkyl halides, potassium metabisulfite, and allylic bromides under ultraviolet irradiation at room temperature is developed. Diverse allylic sulfones are generated in moderate to good yields.

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.

Deaminative metal-free reaction of alkenylboronic acids, sodium metabisulfite and Katritzky salts

2021 ◽  
Author(s):  
Tonghao Zhu ◽  
Jia Shen ◽  
Yuyuan Sun ◽  
Jie Wu
Keyword(s):  
Sodium Metabisulfite ◽  
Metal Free ◽  
Efficient Approach ◽  
Three Component Reaction

A convenient and efficient approach to (E)-alkylsulfonyl olefins via a metal/light-free three-component reaction of alkenylboronic acids, sodium metabisulfite and Katritzky salts is described. This alkylsulfonylation proceeds smoothly with a broad substrate scope, leading to diverse (E)-alkylsulfonyl olefins in moderate to good yields.

scholarly journals New Three-Component Reaction: Novel Formation of a Seven-Membered Ring by the Unexpected Reaction at the γ-Position of the β-Keto Ester.

ChemInform ◽  
2007 ◽  
Vol 38 (36) ◽  
Author(s):  
Hiromichi Fujioka ◽  
Kenichi Murai ◽  
Ozora Kubo ◽  
Yusuke Ohba ◽  
Yasuyuki Kita
Keyword(s):  
Membered Ring ◽  
Keto Ester ◽  
Three Component Reaction ◽  
Unexpected Reaction

Photoinduced synthesis of alkylalkynyl sulfones through a reaction of potassium alkyltrifluoroborates, sulfur dioxide, and alkynyl bromides

2020 ◽  
Vol 7 (7) ◽  
pp. 938-943 ◽  
Author(s):  
Xinxing Gong ◽  
Min Yang ◽  
Jin-Biao Liu ◽  
Fu-Sheng He ◽  
Jie Wu
Keyword(s):  
Sulfur Dioxide ◽  
Visible Light ◽  
Visible Light Irradiation ◽  
Room Temperature ◽  
Light Irradiation ◽  
Sodium Metabisulfite ◽  
Photoinduced Reaction ◽  
Photoinduced Synthesis

A photoinduced reaction of potassium alkyltrifluoroborates, sodium metabisulfite, and alkynyl bromides under visible light irradiation at room temperature is developed.

scholarly journals Unexpected polymerization mechanism of dilignol in the lignin growing

2019 ◽  
Vol 6 (7) ◽  
pp. 190445 ◽  
Author(s):  
Yasuyuki Matsushita ◽  
Yuto Oyabu ◽  
Dan Aoki ◽  
Kazuhiko Fukushima
Keyword(s):  
Reaction Mechanism ◽  
Higher Plants ◽  
Phenoxy Radical ◽  
Covalent Linkage ◽  
Polymerization Mechanism ◽  
Essential Component ◽  
Radical Coupling ◽  
Unexpected Reaction ◽  
Lignin Polymerization ◽  
Dehydrogenative Polymerization

Lignin is an essential component of higher plants, which is built by the enzymatic dehydrogenative polymerization of monolignols. First, monolignol is enzymatically oxidized to produce the phenoxy radical, which can form resonance hybrids. Two radical resonant hybrids are coupled with each other to yield dilignol with various linkage types, of which the main structures are β- O -4′ ( I ), β-5′ ( II ) and β-β′ ( III ). However, the reaction mechanism behind the addition lignol radicals to dilignol is not yet fully understood. Here, we show an unexpected reaction with structure II during enzymatic dehydrogenative polymerization, which involves cleavage of a covalent linkage and creation of a new radical coupling site. This implied that the β-5 dilignol diversifies the growing pattern of lignin. This discovery elucidates a novel mechanism in lignin polymerization.

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