Functionalized α,β-ynones: efficient ligand for Cu catalyzed Sonogashira-type cross-coupling reaction

RSC Advances ◽  
2016 ◽  
Vol 6 (111) ◽  
pp. 109296-109300 ◽  
Author(s):  
Xian Wang ◽  
Zhenhua Wang ◽  
Zunyuan Xie ◽  
Guofang Zhang ◽  
Weiqiang Zhang ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Terminal Alkynes ◽  
Cross Coupling Reactions ◽  
Aryl Iodides ◽  
Cross Coupling Reaction ◽  
The Cross

1,3-Yones as σ-, π-electron donating ligands significantly accelerated the cross-coupling reactions of aryl iodides with terminal alkynes, in which as low as 0.1 to 1 mol% of CuI were efficiently activated.

scholarly journals Synthesis of substituted Z-styrenes by Hiyama-type coupling of oxasilacycloalkenes: application to the synthesis of a 1-benzoxocane

2017 ◽  
Vol 13 ◽  
pp. 2122-2127 ◽  
Author(s):  
James R Vyvyan ◽  
Courtney A Engles ◽  
Scott L Bray ◽  
Erik D Wold ◽  
Christopher L Porter ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Cyclic Ether ◽  
Carbon Skeleton ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Aryl Iodides ◽  
Cross Coupling Reaction ◽  
Type Coupling ◽  
The Cross

Several Hiyama cross-coupling reactions of oxasilacycloalkenes and aryl iodides are described that produce trisubstituted Z-styrenes in moderate to excellent yields. Both electron-rich and electron-poor aryl iodides are tolerated in the cross-coupling reaction. The oxasilacycloalkene coupling partners were prepared by ruthenium-catalyzed intramolecular anti-hydrosilylation of alkynols. One of the cross-coupling products was converted to a 1-benzoxocane, albeit in low yield, using an intramolecular Buchwald–Hartwig etherification. The cyclic ether produced contains the carbon skeleton of heliannuol A.

Copper-catalyzed arylation of biguanide derivatives via C–N cross-coupling reactions

2015 ◽  
Vol 13 (47) ◽  
pp. 11432-11437 ◽  
Author(s):  
Chen Zhang ◽  
Bo Huang ◽  
Ai-Qing Bao ◽  
Xiao Li ◽  
Shunna Guo ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Mild Conditions ◽  
Cross Coupling Reactions ◽  
Aryl Iodides ◽  
Cross Coupling Reaction

We developed an efficient copper-catalyzed cross-coupling reaction of biguanide hydrochloride derivatives with both aryl iodides and bromides under mild conditions.

scholarly journals Highly efficient synthesis of 2-substituted benzo[b]furan derivatives from the cross-coupling reactions of 2-halobenzo[b]furans with organoalane reagents

Synthesis ◽  
2021 ◽  
Author(s):  
chang wen ◽  
Qing Han Li ◽  
Chuan Wu ◽  
ruiqiang Luo ◽  
Feng Chen
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Practical Method ◽  
Bioactive Molecules ◽  
Coupling Reactions ◽  
Highly Efficient ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
The Cross

A highly efficient and simple route for the synthesis of 2-substituted benzo[b]furans has been developed by Palladium catalyzed the cross-coupling reaction of 2-halobenzo[b]furans with aryl, alkynyl and alkylaluminum reagents. Various 2-aryl, 2-alkynyl and 2-alkyl substituted benzo[b]furans derivatives can be obtained with 23-97% isolated yields using 2-3 mol% PdCl2/ 4-6 mol% XantPhos as the catalyst under mild reaction conditions. The aryls bearing electron-donating or electron-withdrawing groups in 2-halobenzo[b]furans gave products in 40-97% isolated yields. In addition, aluminum reagents containing thienyl, furanyl trimethylsilanyl and benzyl groups worked efficiently with 2-halobenzo[b]furans as well, and three bioactive molecules with 2-substituted benzo[b]furan skeleton were synthesized. Furthermore, the broad substrates scope and the typical maintenance of vigorous efficiency on gram scale make this protocol a potentially practical method to synthesize 2-substituted benzo[b]furans derivatives. On the basis of the experimental results, a possible catalytic cycle has been proposed.

An Iron-Based Catalyst Enables The Enantioconvergent Synthesis of Chiral 1,1-Diarylalkanes Through a Suzuki-Miyaura Cross-Coupling Reaction

2020 ◽  
Author(s):  
Chet Tyrol ◽  
Nang Yone ◽  
Connor Gallin ◽  
Jeffery Byers
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Radical Intermediates ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Boronic Esters ◽  
Carbon Centered Radical ◽  
Iron Based ◽  
High Yields

By using an iron-based catalyst, access to enantioenriched 1,1-diarylakanes was enabled through an enantioselective Suzuki-Miyaura crosscoupling reaction. The combination of a chiral cyanobis(oxazoline) ligand framework and 1,3,5-trimethoxybenzene additive were essential to afford high yields and enantioselectivities in cross-coupling reactions between unactivated aryl boronic esters and a variety of benzylic chlorides, including challenging ortho-substituted benzylic chloride substrates. Mechanistic investigations implicate a stereoconvergent pathway involving carbon-centered radical intermediates.

The Synthesis of Pharmaceuticals: The Effective Application of Secondary Boronic Esters in Enantioselective Suzuki ‐ Miyaura Cross ‐ Coupling Reactions

2016 ◽  
Author(s):  
Jonathon Moir
Keyword(s):  
Natural Products ◽  
Human Life ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Boronic Esters ◽  
Carbon Carbon Bonds ◽  
Effective Drugs

Pharmaceuticals and drugs have become an indispensable part of human life. Presently, a myriad of different drugs are available for a variety of mental and physical health concersn. The synthesis of these drugs, however, remains an elusive and often difficult aspect of the industry. The importance of chirality, or "handedness", in the synthesis of natural products is paramount, as any given pair of enantiomers can have widely differing physiological effects. As such, the ability to control the enantioselectivity of a reaction is of the utmost importance. One example of a facile method used to form carbon-carbon bonds is the Suzuki-Miyaura cross-coupling reaction. Not only is this reaction effective at coupling primary organoboronic esters with organohalides, but recent work in the Crudden group in the Department of Chemistry has revealed an effective method of also cross-couplingchiral secondary organoboronic esters with good retention of stereochemistry. This work, the first of its kind, is crucial in developing single-handed natural products for a wide array of applications, including applications in the pharmaceutical industry. The end result is safer and more effective drugs for distribution to the general public. To expand the scope of this project, new substrates are currently being synthesized for cross-coupling applications. The overall goal is to improve upon current methodologies, while helping to meet the industrial and academic needs of the future.  

Regiospecific Palladium-Catalyzed Cross-Coupling Reactions Using the Operational Equivalent of 1,3-Dilithiopropyne

Synthesis ◽  
2020 ◽  
Vol 52 (16) ◽  
pp. 2387-2394 ◽  
Author(s):  
Jorge A. Cabezas ◽  
Natasha Ferllini
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Terminal Alkyne ◽  
Copper Iodide ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
High Yields

A regiospecific palladium-catalyzed cross-coupling reaction using the operational equivalent of the dianion 1,3-dilithiopropyne, with aromatic iodides is reported. This reaction gives high yields of 1-propyn-1-yl-benzenes and 2-(propyn-1-yl)thiophenes in the presence of catalytic amounts of palladium(0) or (II) and stoichiometric amounts of copper iodide. No terminal alkyne or allene isomers were detected. Reaction conditions were very mild and several functional groups were tolerated.

scholarly journals Synthesis of 4-Alkyl-4H-1,2,4-triazole Derivatives by Suzuki Cross-coupling Reactions and Their Luminescence Properties

Molecules ◽  
2019 ◽  
Vol 24 (3) ◽  
pp. 652 ◽  
Author(s):  
Monika Olesiejuk ◽  
Agnieszka Kudelko ◽  
Marcin Swiatkowski ◽  
Rafal Kruszynski
Keyword(s):  
Ionic Liquids ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Luminescence Properties ◽  
Coupling Reactions ◽  
Triazole Derivatives ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Derivatives Of

New derivatives of 4-alkyl-3,5-diaryl-4H-1,2,4-triazole were synthesized utilizing the Suzuki cross-coupling reaction. The presented methodology comprises of the preparation of bromine-containing 4-alkyl-4H-1,2,4-triazoles and their coupling with different commercially available boronic acids in the presence of ionic liquids or in conventional solvents. The obtained compounds were tested for their luminescence properties.

Application of a 2-aryl indenylphosphine ligand in the Buchwald–Hartwig cross-coupling reactions of aryl and heteroaryl chlorides under the solvent-free and aqueous conditions

2017 ◽  
Vol 15 (27) ◽  
pp. 5805-5810 ◽  
Author(s):  
Yan Liu ◽  
Jia Yuan ◽  
Zi-Fei Wang ◽  
Si-Hao Zeng ◽  
Meng-Yue Gao ◽  
...  
Keyword(s):  
Catalytic System ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Solvent Free ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Aqueous Conditions

An efficient solvent-free and aqueous protocol for the Buchwald–Hartwig cross-coupling reaction has been developed. Notably, the catalytic system also efficiently catalyzed the reaction under aqueous conditions.

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