189828-30-6Relevant articles and documents
Synthesis and application of N-heterocyclic carbene-palladium ligands with glycerol dendrons for the Suzuki-Miyaura cross-coupling in water
Lukowiak, Maike C.,Meise, Markus,Haag, Rainer
, p. 2161 - 2165 (2014)
Highly active glycerol-dendron-supported N-heterocyclic carbene-palladium catalysts with catalytic sites at the core position were obtained with an efficient modular synthesis. A symmetrical ligand structure was designed to build a larger microenvironment by increasing the number of dendron generations. The catalytic activity was tested in Suzuki-Miyaura cross-coupling reactions. Deprotection of the dendritic supported catalysts allowed the catalytic reaction to take place in neat water, which is highly desirable for a more sustainable processing. A positive dendritic effect was observed for coupling of activated and nonactivated bromoaryls. Georg Thieme Verlag Stuttgart. New York.
Palladium-catalyzed borylation of aryl bromides and chlorides using phosphatrioxa-adamantane ligands
Lamola, Jairus L.,Moshapo, Paseka T.,Holzapfel, Cedric W.,Christopher Maumela, Munaka
, (2021/12/13)
Catalysts based on the combination of Pd(OAc)2 and the electron-deficient phosphatrioxa-adamantane ligands are described for borylation of aryl bromides and chlorides. Catalytic evaluation of a small library of phosphatrioxa-adamantane ligands provided some insights on the preferred ligand steric profile for borylation reactions. The corresponding aryl boronate esters were accessed under mild conditions (25–70 °C) and isolated in high yields (up to 96%).
Suzuki-Miyaura coupling catalyzed by a Ni(II) PNP pincer complex: Scope and mechanistic insights
Madera, Justin,Slattery, Megan,Arman, Hadi D.,Tonzetich, Zachary J.
, (2020/02/04)
The nickel(II) pincer complex, [NiCl(PhPNP)] (PhPNP = anion of 2,5-bis(diphenylphosphinomethyl)pyrrole), has been employed as a precatalyst for the Suzuki-Miyaura cross-coupling reaction of aryl halides and boronic acids. Both electron-rich and electron-deficient aromatic bromides were found to undergo coupling with boronic acids in modest yield at elevated temperature in the presence of K3PO4·H2O. Preliminary mechanistic studies of the reaction identified a novel species formulated as the boronate complex, [Ni(OB{OH}{2-tolyl})(PhPNP)], which most likely represents a catalyst deactivation pathway. The productive catalytic cycle was found to be most consistent with a Ni(I)/Ni(III) process where the boronic acid serves as both reductant and nucleophile in the presence of base.
Method for synthesizing biphenyl compound by taking phenol as raw material
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Paragraph 0062-0064, (2020/07/15)
The invention discloses a method for synthesizing a biphenyl compound by using phenol as a raw material in the technical field of organic chemical synthesis, which comprises the following steps: carrying out a mixed reaction process on phenol or substituted phenol, alkali and 50-90% ethanol aqueous solution, slowly introducing sulfonyl fluoride gas, and carrying out magnetic stirring reaction at normal temperature for 4-12 hours, adding arylboronic acid, alkali and a palladium catalyst into a round-bottom flask, continuing to react for 6-12 hours at normal temperature, after the reaction is finished, adding a saturated edible salt solution into the round-bottom flask, carrying out a water quenching reaction process to obtain a reaction mixture, extracting a reaction product from the reaction mixture by using ethyl acetate, combining organic phases, concentrating filtrate, and separating the concentrated filtrate by using column chromatography to obtain analytically pure biphenyl or terphenyl compounds. By using the method, on one hand, the production cost of the biphenyl compound is reduced, and on the other hand, the method also has a wide application prospect in the aspects of synthesis of natural products, medicines, pesticides, herbicides, polymer conduction materials, liquid crystal materials and the like.
