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.

Transition-Metal-Free Synthesis of Thiosulfonates through Radical Coupling Reaction

Synlett ◽  
2018 ◽  
Vol 29 (15) ◽  
pp. 2076-2080 ◽  
Author(s):  
Wen-Ting Wei ◽  
Zhiyong Guo ◽  
Guodong Zhou ◽  
Xu-Dong Xu ◽  
Gan-Ping Chen
Keyword(s):  
Transition Metal ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Mechanistic Studies ◽  
Reaction Conditions ◽  
Coupling Process ◽  
Metal Free ◽  
Radical Coupling ◽  
Radical Coupling Reaction ◽  
High Yields

An efficient and practical transition-metal-free radical ­coupling reaction of sulfonyl hydrazides mediated by NIS/K2S2O8 has been developed to afford a variety of biological activity thiosulfonates in moderate to excellent yields. Compared to a known approach for the synthesis of thiosulfonates from sulfonyl hydrazides, this strategy features high yields, mild reaction conditions, and broad substrate scope. The mechanistic studies revealed that the procedure undergoes via a radical cross-coupling process for the construction of S–S bonds.

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.

Synthesis of block and star copolymers by photoinduced radical coupling process

2009 ◽  
Vol 47 (11) ◽  
pp. 2938-2947 ◽  
Author(s):  
Gokhan Temel ◽  
Binnur Aydogan ◽  
Nergis Arsu ◽  
Yusuf Yagci
Keyword(s):  
Coupling Process ◽  
Radical Coupling ◽  
Star Copolymers

scholarly journals SET activation of nitroarenes by 2-azaallyl anions as a straightforward access to 2,5-dihydro-1,2,4-oxadiazoles

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Dong Zou ◽  
Lishe Gan ◽  
Fan Yang ◽  
Huan Wang ◽  
Youge Pu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Experimental Evidence ◽  
Radical Anion ◽  
Reaction Pathway ◽  
Cycloaddition Reaction ◽  
Electron Donors ◽  
Ring Closure ◽  
Computational Studies ◽  
Metal Free ◽  
Radical Coupling

AbstractThe use of nitroarenes as amino sources in synthesis is challenging. Herein is reported an unusual, straightforward, and transition metal-free method for the net [3 + 2]-cycloaddition reaction of 2-azaallyl anions with nitroarenes. The products of this reaction are diverse 2,5-dihydro-1,2,4-oxadiazoles (>40 examples, up to 95% yield). This method does not require an external reductant to reduce nitroarenes, nor does it employ nitrosoarenes, which are often used in N–O cycloadditions. Instead, it is proposed that the 2-azaallyl anions, which behave as super electron donors (SEDs), deliver an electron to the nitroarene to generate a nitroarene radical anion. A downstream 2-azaallyl radical coupling with a newly formed nitrosoarene is followed by ring closure to afford the observed products. This proposed reaction pathway is supported by computational studies and experimental evidence. Overall, this method uses readily available materials, is green, and exhibits a broad scope.

Transition metal-free, visible-light-mediated construction of α,β-diamino esters via decarboxylative radical addition at room temperature

2019 ◽  
Vol 6 (13) ◽  
pp. 2245-2249 ◽  
Author(s):  
Guibing Wu ◽  
Jingwen Wang ◽  
Chengyu Liu ◽  
Maolin Sun ◽  
Lei Zhang ◽  
...  
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Carboxylic Acids ◽  
Room Temperature ◽  
Radical Addition ◽  
Metal Free ◽  
Radical Coupling

A metal-free photoredox catalyzed decarboxylative radical coupling of free-carboxylic acids and glyoxylic oximes was developed to synthesize α,β-diamino acids.

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.

Recent Developments in Transition-Metal-Free Functionalization and Derivatization Reactions of Pyridines

Synlett ◽  
2020 ◽  
Author(s):  
Lei Jiao ◽  
Fei-Yu Zhou
Keyword(s):  
Transition Metal ◽  
Structural Motif ◽  
Metal Exchange ◽  
Coupling Reactions ◽  
Phosphonium Salts ◽  
Metal Free ◽  
Radical Coupling ◽  
In Situ Activation ◽  
Recent Developments

AbstractPyridine is an important structural motif that is prevalent in natural products, drugs, and materials. Methods that functionalize and derivatize pyridines have gained significant attention. Recently, a large number of transition-metal-free reactions have been developed. In this review, we provide a brief summary of recent advances in transition-metal-free functionalization and derivatization reactions of pyridines, categorized according to their reaction modes.1 Introduction2 Metalated Pyridines as Nucleophiles2.1 Deprotonation2.2 Halogen–Metal exchange3 Activated Pyridines as Electrophiles3.1 Asymmetric 2-Allylation by Chiral Phosphite Catalysis3.2 Activation of Pyridines by a Bifunctional Activating Group3.3 Alkylation of Pyridines by 1,2-Migration3.4 Alkylation of Pyridines by [3+2] Addition3.5 Pyridine Derivatization by Catalytic In Situ Activation Strategies3.6 Reactions via Heterocyclic Phosphonium Salts4 Radical Reactions for Pyridine Functionalization4.1 Pyridine Functionalization through Radical Addition Reactions4.2 Pyridine Functionalization through Radical–Radical Coupling Reactions5 Derivatization of Pyridines through the Formation of Meisenheimer-Type Pyridyl Anions6 Conclusion

Transition-metal-free cleavage of C–C double bonds: a three-component reaction of aromatic alkenes with S8and amides towards aryl thioamides

2018 ◽  
Vol 5 (22) ◽  
pp. 3315-3318 ◽  
Author(s):  
Lantao Liu ◽  
Zhanghong Guo ◽  
Kai Xu ◽  
Shuangshuang Hui ◽  
Xiaofang Zhao ◽  
...  
Keyword(s):  
Transition Metal ◽  
Double Bonds ◽  
Metal Free ◽  
Three Component Reaction

A novel transition-metal-free cleavage of C–C double bonds has been developed from a three-component reaction involving aromatic alkenes, S8and amides, generating various aryl thioamides in up to 96% yields.

Metal-free deoxygenative sulfonylation of quinoline N-oxides with sodium sulfinates via a dual radical coupling process

2018 ◽  
Vol 5 (17) ◽  
pp. 2604-2609 ◽  
Author(s):  
Long-Yong Xie ◽  
Sha Peng ◽  
Fang Liu ◽  
Guan-Rong Chen ◽  
Wen Xia ◽  
...  
Keyword(s):  
Coupling Process ◽  
Metal Free ◽  
Radical Coupling

The first example of a metal- and reductant-free deoxygenative sulfonylation of quinoline N-oxides with sodium sulfinates via a dual radical coupling process is reported.

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.

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