39117-68-5Relevant academic research and scientific papers
THE PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF MESITYLCOPPER WITH ARYL IODIDES
Bumagin, N. A.,Kalinovskii, I. O.,Beletskaya, I. P.
, p. C1 - C3 (1984)
Mesitylcopper reacts with aryl iodides containing both electron-withdrawing and electron-donating groups in the presence of 1 equivalent Bu4NX (X = Br, I) and 1 mol.percent of PhPdI(PPh3)2 to give cross-coupling products in high yields.
Investigations into ambient temperature biaryl coupling reactions
Anderson, James C.,Namli, Hilmi,Roberts, Craig A.
, p. 15123 - 15134 (1997)
An ambient temperature, unsymmetrical, biaryl coupling reaction for hindered systems based on Suzuki methodology has been developed. A description of the optimisation of this process leading to the recommendation of aqueous thallium hydroxide as base, in dimethylacetamide, with hindered boronic acids and aryl halides to achieve good to moderate yields of hindered biaryls is presented, along with an interpretation of the reaction conditions. The yields of hindered Stille biaryl coupling reactions seemed to be little enhanced by the use of less coordinating ligands such as tri-2-furylphosphine and triphenylarsine.
Pyrazole-Mediated C-H Functionalization of Arene and Heteroarenes for Aryl-(Hetero)aryl Cross-Coupling Reactions
Kundu, Abhishek,Dey, Dhananjay,Pal, Subhankar,Adhikari, Debashis
, p. 15665 - 15673 (2021/11/16)
Herein we introduce a transition-metal-free protocol that involves a commercially available, inexpensive pyrazole molecule to conduct C-C cross-coupling reactions at room temperature via a radical pathway. Using this method, an aryldiazonium salt has been coupled to a wide range of arenes and heteroarenes including benzene, mesitylene, thiophene, furan, benzoxazole to result the corresponding biaryl products. The full reaction mechanism is elucidated along with the crystallographic probation of an active initiator species. A potassium-stabilized deprotonated pyrazole steers single-electron transfer to the substrate and behaves as an initiator for the reaction.
Copper catalysed Gomberg-Bachmann-Hey reactions of arenediazonium tetrafluoroborates and heteroarenediazonium o-benzenedisulfonimides. Synthetic and mechanistic aspects
Antenucci, Achille,Barbero, Margherita,Dughera, Stefano,Ghigo, Giovanni
, (2020/10/20)
Gomberg-Bachmann-Hey reactions were carried out in the presence of copper as a catalyst and gave rise to biaryls or heterobiaryls in good yields and in mild reaction conditions. A computational study of some key points of the reaction was performed. The results are coherent with the experimental data and confirm some aspects of the mechanism. The reaction free energies for the reduction in benzene by CuI of a set of 40 (hetero)arenediazonium tetrafluoroborates were calculated. Both the experiments and the calculations showed that in the coupling with substituted solvents (toluene, bromobenzene, nitrobenzene and anisole) the binding to the ortho position was always favoured.
Probing Peripheral H-Bonding Functionalities in BN-Doped Polycyclic Aromatic Hydrocarbons
Tasseroul, Jonathan,Lorenzo-Garcia, Maria Mercedes,Dosso, Jacopo,Simon, Fran?ois,Velari, Simone,De Vita, Alessandro,Tecilla, Paolo,Bonifazi, Davide
, p. 3454 - 3464 (2020/03/04)
The replacement of carbon atoms at the zigzag periphery of a benzo[fg]tetracenyl derivative with an NBN atomic triad allows the formation of heteroatom-doped polycyclic aromatic hydrocarbon (PAH) isosteres, which expose BN mimics of the amidic NH function
Phenalenyl Based Aluminum Compound for Catalytic C-H Arylation of Arene and Heteroarenes at Room Temperature
Vardhanapu, Pavan K.,Ahmed, Jasimuddin,Jose, Anex,Shaw, Bikash Kumar,Sen, Tamal K.,Mathews, Amita A.,Mandal, Swadhin K.
, p. 289 - 299 (2019/01/10)
Main group metal based catalysis has been considered to be a cost-effective alternative way to the transition metal based catalysis, due to the high abundance of main group metals in the Earth's crust. Among the main group metals, aluminum is the most abundant (7-8%) in the Earth's crust, making the development of aluminum based catalysts very attractive. So far, aluminum based compounds have been popularly used as Lewis acids in a variety of organic reactions, but chemical transformation demanding a redox based process has never utilized an Al(III) complex as a catalyst. Herein, we tuned the redox noninnocence behavior of a phenalenyl ligand by coupling with Al(III) ion, which subsequently can store the electron upon reduction with K to carry out direct C-H arylation of heteroarenes/mesitylene at ambient temperature. A mechanistic investigation revealed that a three-electron reduced phenalenyl based triradical aluminum(III) complex plays the key role in such catalysis. The electronic structure of the catalytically active triradical species has been probed using EPR spectroscopy, magnetic susceptibility measurements, and electronic structure calculations using a DFT method.
Perylenequinonoid-catalyzed photoredox activation for the direct arylation of (het)arenes with sunlight
Zhang, Shiwei,Tang, Zhaocheng,Bao, Wenhao,Li, Jia,Guo, Baodang,Huang, Shuping,Zhang, Yan,Rao, Yijian
supporting information, p. 4364 - 4369 (2019/05/10)
Naturally occurring perylenequinonoid pigments (PQPs) have attracted considerable attention owing to their excellent properties of photosensitization. They have been widely investigated as an aspect of photophysics and photobiology. However, their applications in photocatalysis are yet to be explored. We report here that sunlight along with 1 mol% cercosporin, which is one of the perylenequinonoid pigments, catalyzes the direct C-H bond arylation of (het)arenes by a photoredox process with good regioselectivity and broad functional group compatibility. Furthermore, a gram-scale reaction with great conversions of substrates was achieved even by a cercosporin-containing supernatant without organic solvent extraction and purification after liquid fermentation. Thus we set up a bridge between microbial fermentation and organic photocatalysis for chemical reactions in a sustainable, environmentally friendly manner.
GLUCAGON RECEPTOR ANTAGONISTS
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Paragraph 0249; 0251; 0259; 0260, (2019/09/04)
Provided herein are solid state forms of compounds, including enantiomerically pure forms thereof, and pharmaceutically acceptable salts or co-crystals and prodrugs thereof which have glucagon receptor antagonist or inverse agonist activity. Further, provided herein are pharmaceutical compositions and methods of treating, preventing, ameliorating, delaying the time to onset or reducing the risk for the development or progression of at least one condition, disease, or disorder for which one or more glucagon receptor antagonist is indicated, including Type I and II diabetes, insulin resistance, hyperglycemia, ketoacidosis, or ketosis.
An Iron-Based Long-Lived Catalyst for Direct C?H Arylation of Arenes and Heteroarenes
Chakraborty, Soumi,Ahmed, Jasimuddin,Shaw, Bikash Kumar,Jose, Anex,Mandal, Swadhin K.
, p. 17651 - 17655 (2018/11/10)
Direct C?H arylation of arenes and heteroarenes to biaryls at ambient temperature has been accomplished using a phenalenyl-supported iron(III) catalyst. The present catalyst requires a chemical reductant such as potassium and functions without any light stimulation. C?H arylation of various heteroarenes including pyridine as well as unactivated arene such as benzene delivered good to excellent yield (28 examples, up to 92 %) at room temperature. A combined effort based on experiments and theoretical calculations established that a phenalenyl-based radical species (generated by chemical reduction of the iron(III) coordinated phenalenyl complex) plays key role during the catalysis. Furthermore, this catalyst displayed remarkable stability during the catalysis, as evident from the fact that it was still usable over ten consecutive catalytic runs without losing its catalytic efficiency.
Integrating Organic Lewis Acid and Redox Catalysis: The Phenalenyl Cation in Dual Role
Ahmed, Jasimuddin,Chakraborty, Soumi,Jose, Anex,Sreejyothi,Mandal, Swadhin K.
supporting information, p. 8330 - 8339 (2018/06/19)
In recent years, merging different types of catalysis in a single pot has drawn considerable attention and these catalytic processes have mainly relied upon metals. However, development of a completely metal free approach integrating organic redox and organic Lewis acidic property into a single system has been missing in the current literature. This study establishes that a redox active phenalenyl cation can activate one of the substrates by single electron transfer process while the same can activate the other substrate by a donor-acceptor type interaction using its Lewis acidity. This approach has successfully achieved light and metal-free catalytic C-H functionalization of unactivated arenes at ambient temperature (39 entries, including core moiety of a top-selling molecule boscalid), an economically attractive alternative to the rare metal-based multicatalysts process. A tandem approach involving trapping of reaction intermediates, spectroscopy along with density functional theory calculations unravels the dual role of phenalenyl cation.
