2,5-Dihydroxyterephthalic Acid Accelerated Cu(NO3)2.3H2O-Catalyzed Homocoupling Reaction of Arylboronic Acids

2020 ◽  
Vol 17 (11) ◽  
pp. 877-883
Author(s):  
Fengtian Wu ◽  
Chenlong Nan ◽  
Jianwei Xie ◽  
Mingyang Ma
Keyword(s):  
Good Yield ◽  
Functional Group ◽  
Catalyst System ◽  
Arylboronic Acids ◽  
Convenient Approach ◽  
Homocoupling Reaction

A catalyst system derived from commercially available Cu(NO3)2.3H2O and 2,5- dihydroxyterephthalic acid is applied to the homocoupling reaction of arylboronic acids. This transformation provides a convenient approach to symmetrical biaryls with good to excellent yields (39%- 95%), and exhibits good functional group compatibility. Furthermore, biaryl can be prepared in gram quantities in good yield.

scholarly journals Synthesis of 3-Aryl-1-Indanones via CsF-Promoted Coupling of Arylboronic Acids with N-Tosylhydrazones

2018 ◽  
Vol 42 (1) ◽  
pp. 40-43 ◽  
Author(s):  
Yueqiang Liu ◽  
Lingjuan Chen ◽  
Yan Liu ◽  
Ping Liu ◽  
Bin Dai
Keyword(s):  
Good Yield ◽  
Functional Group ◽  
Cross Coupling ◽  
Arylboronic Acid ◽  
Arylboronic Acids

A series of 173-aryl-1-indanones, four of which are novel, were prepared in good yield via a CsF-promoted reductive cross-coupling of the monotosylhydrazone of a 1,3-indanedione with an arylboronic acid. The method demonstrates wide substrate scope and good functional group tolerance. Moreover, the 3-aryl-1-indanones could also be prepared on a multi-gram scale.

Identification of a Surprising Boronic Acid Homocoupling Process in Suzuki–Miyaura Cross-Coupling Reactions Utilizing a Hindered Fluorinated Arene

Synlett ◽  
2020 ◽  
Author(s):  
Samantha L. Gargaro ◽  
Bre'Shon Dunson ◽  
Joshua D. Sieber
Keyword(s):  
Boronic Acid ◽  
Good Yield ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Product Formation ◽  
Coupling Reactions ◽  
Arylboronic Acids ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Homocoupling Reaction

AbstractThe Suzuki–Miyaura cross-coupling reaction of 2-bromo-1,3-bis(trifluoromethyl)benzene with arylboronic acids was evaluated and determined to suffer from the formation of large amounts of boronic acid homocoupling products in conjunction with dehalogenation. Homocoupling product formation in this process likely occurs through a rare protonolysis/second transmetalation event rather than by the well-established mechanism requiring the involvement of O2. The scope of this boronic acid homocoupling reaction was investigated and shown to predominate with electron-deficient arylboronic acids. Finally, a good yield of cross-coupling products could be obtained by employing dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (SPhos) as the ligand.

Nickel-Catalyzed Inter- and Intramolecular Carbon-Sulfur Bond Metathesis by Reversible Arylation

2019 ◽  
Author(s):  
Tristan Delcaillau ◽  
Alessandro Bismuto ◽  
Zhong Lian ◽  
Bill Morandi
Keyword(s):  
Good Yield ◽  
Functional Group ◽  
Product Formation ◽  
Single Bond ◽  
Ring Closing Metathesis ◽  
Catalytic Systems ◽  
Metathesis Reactions ◽  
New Applications ◽  
Further Development ◽  
Sulfur Bond

A nickel-catalyzed carbon-sulfur bond metathesis has been developed to access high-value thioethers. 1,2-bis(dicyclohexylphosphino)ethane (dcype) is essential to promote this highly functional group tolerant reaction. Further, synthetically challenging macrocycles could be obtained in good yield in an unusual example of ring-closing metathesis which does not involve alkene bonds. In-depth organometallic studies support a reversible Ni(0)-Ni(II) pathway to product formation. Overall, this work does not only disclose a more sustainable and more functional group tolerant alternative to previous catalytic systems based on Pd, but also presents new applications and mechanistic information which are highly relevant to the further development and application of unusual single bond metathesis reactions.

Facile Access to Triazole-Fused 3,1-Benzoxazines Enabled by Metal-Free Base-Promoted Intramolecular C–O Coupling

Synthesis ◽  
2021 ◽  
Author(s):  
Yury N. Kotovshchikov ◽  
Stepan S. Tatevosyan ◽  
Gennadij V. Latyshev ◽  
Nikolay V. Lukashev ◽  
Irina P. Beletskaya
Keyword(s):  
Transition Metal ◽  
Functional Group ◽  
Cost Effective ◽  
Reductive Cleavage ◽  
Effective Procedure ◽  
Free Base ◽  
Metal Free ◽  
Fused Heterocycles ◽  
Convenient Approach

AbstractA convenient approach to assemble 1,2,3-triazole-fused 4H-3,1-benzoxazines has been developed. Diverse alcohol-tethered 5-iodotriazoles, readily accessible by a modified protocol of Cu-catalyzed (3+2)-cycloaddition, were utilized as precursors of the target fused heterocycles. The intramolecular C–O coupling proceeded efficiently under base-mediated transition-metal-free conditions, furnishing cyclization products in yields up to 96%. Suppression of the competing reductive cleavage of the C–I bond was achieved by the use of Na2CO3 in acetonitrile at 100 °C. This practical and cost-effective procedure features a broad substrate scope and valuable functional group tolerance.

Rapid Ligand-Free Base-Accelerated Copper-Catalyzed Homocoupling Reaction of Arylboronic Acids

Synlett ◽  
2016 ◽  
Vol 28 (05) ◽  
pp. 601-606 ◽  
Author(s):  
Feng Gao ◽  
Xian-Li Zhou ◽  
Ya-Nan Cao ◽  
Xin-Chuan Tian ◽  
Xing-Xiu Chen ◽  
...  
Keyword(s):  
Free Base ◽  
Arylboronic Acids ◽  
Ligand Free ◽  
Homocoupling Reaction

Visible-Light-Induced Radical Polynitration of Arylboronic Acids: Synthesis of Polynitrophenols

Synthesis ◽  
2018 ◽  
Vol 50 (15) ◽  
pp. 2891-2896 ◽  
Author(s):  
Jinna Song ◽  
Xihe Bi ◽  
Qi Zhang ◽  
Kaki Raveendra Babu ◽  
Zhouliang Huang
Keyword(s):  
Visible Light ◽  
Aromatic Compounds ◽  
Functional Group ◽  
Simple Procedure ◽  
One Pot ◽  
Arylboronic Acids ◽  
Mild Conditions ◽  
Conventional Methods ◽  
Straightforward Approach

We report a visible light-assisted one-pot method for the synthesis of polynitrophenols through radical tandem hydroxylation and nitration of arylboronic acids by utilizing copper(II) nitrate tri­hydrate as the nitro source. This method features mild conditions, a simple procedure, and good functional group tolerance. Compared to conventional methods, this work provides a straightforward approach for the polynitration of aromatic compounds.

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