16419-60-6Relevant articles and documents
Deprotection of pinacolyl boronate esters via hydrolysis of intermediate potassium trifluoroborates
Yuen, Alexander K.L.,Hutton, Craig A.
, p. 7899 - 7903 (2005)
An efficient two-step procedure for the deprotection of pinacolyl organoboronate esters is described. Reaction with excess potassium hydrogen fluoride produces the corresponding stable, crystalline potassium organotrifluoroborate salts. Treatment of the trifluoroborates with either inorganic base or trimethylsilyl chloride and water affords the corresponding organoboronic acid in high yield.
Asymmetric construction of chiral C-N axes through rhodium-catalyzed 1,4-addition
Duan, Wei-Liang,Imazaki, Yusuke,Shintani, Ryo,Hayashi, Tamio
, p. 8529 - 8536 (2007)
Catalytic asymmetric construction of chiral C-N axes has been developed through a rhodium-catalyzed asymmetric 1,4-addition reaction. Both central chirality and axial chirality have been controlled at the same time using Rh/(R,R)-Ph-bod* catalyst with high enantio- and diastereoselectivity. This method has also been applied to the preparation of a planar-chiral ferrocene derivative. The resulting chiral C-N axis can be used as a good template to control the stereochemistry in the subsequent transformations such as alkylation and Diels-Alder reactions.
Aryllead triacetates in the synthesis of oxaphenanthrene derivatives
Fedorov, Alexey Yu,Carrara, Fabien,Finet, Jean-Pierre
, p. 5875 - 5877 (2001)
Ortho-Halomethylphenyllead triacetates (halo = bromine or chlorine) react with phenols in the presence of triethylamine and a pyridine derivative to afford modest to good yields of dibenzo[b,d]-6H-pyrans.
Structure, conformation, and dynamic processes of the stereolabile atropisomers of hindered terphenyl hydrocarbons
Lunazzi, Lodovico,Mazzanti, Andrea,Minzoni, Mirko,Edgar Anderson
, p. 1291 - 1294 (2005)
(Chemical Equation Presented) Ortho-substituted p-terphenyl hydrocarbons exist as trans and cis atropisomers that were identified by low-temperature NMR spectroscopy. The interconversion barriers increase with the dimensions of the ortho substituents, the experimental values being matched by ab initio calculations. X-ray diffraction shows that only the trans atropisomer is present in the solids. Spectra of a tert-butyl derivative in nonequilibrium conditions indicate that the cis is more populated than the trans atropisomer in solution, favored by attractive interactions.
Method for synthesizing sodium 2-carboxyphenylborate
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Paragraph 0020-0021, (2020/06/17)
The invention discloses a method for synthesizing sodium 2-carboxyphenylborate. The method comprises the following two steps of: 1) taking methyl 2-bromobenzoate as an initial raw material, through bromine removal by butyl lithium, carrying out a one-pot reaction with triisopropyl borate or trimethyl borate to obtain a product 2-methoxycarbonyl phenylboronic acid, and 2) hydrolyzing the 2-methoxycarbonyl phenylboronic acid in a sodium hydroxide methanol solution, and pulping with acetone to obtain sodium 2-carboxyphenylborate monohydrate. The method has the advantages of easily available raw materials, simple operation, safety, environmental protection, low cost and high yield.
Aryl boronic acid preparation method
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Paragraph 0033-0036, (2020/01/25)
The invention belongs to the technical field of fine chemical engineering, and relates to an aryl boronic acid preparation method. In the prior art, aryl boronic acid as a novel safe and environmentally-friendly arylation reagent is widely used in scientific research and production of various fine chemicals containing aryl structures in the fields of medicines, pesticides, advanced materials and the like; and the aryl boronic acid compound preparation method reported in the disclosed literature has problems of harsh reaction conditions and high cost. A purpose of the invention is to provide amethod, wherein an aryl boron compound is formed by carrying out a reaction on a Grignard reagent and trialkyl borate under mild conditions, the composition of the aryl boron compound is converted from the main component diaryl borate into the main component aryl borate, and the aryl borate is hydrolyzed to obtain aryl boric acid, so that the preparation cost of the acyl aryl boric acid compound can be remarkably reduced, and the method has good practical application prospect.
Bedford-type palladacycle-catalyzed miyaura borylation of aryl halides with tetrahydroxydiboron in water
Zernickel, Anna,Du, Weiyuan,Ghorpade, Seema A.,Sawant, Dinesh N.,Makki, Arwa A.,Sekar, Nagaiyan,Eppinger, J?rg
, p. 1842 - 1851 (2018/02/23)
A mild aqueous protocol for palladium catalyzed Miyaura borylation of aryl iodides, aryl bromides and aryl chlorides with tetrahydroxydiboron (BBA) as a borylating agent is developed. The developed methodology requires low catalyst loading of Bedford-type palladacycle catalyst (0.05 mol %) and works best under mild reaction conditions at 40 °C in short time of 6 h in water. In addition, our studies show that for Miyaura borylation using BBA in aqueous condition, maintaining a neutral reaction pH is very important for reproducibility and higher yields of corresponding borylated products. Moreover, our protocol is applicable for a broad range of aryl halides, corresponding borylated products are obtained in excellent yields up to 93% with 29 examples demonstrating its broad utility and functional group tolerance.
Asymmetric Arylation of Imines Catalyzed by Heterogeneous Chiral Rhodium Nanoparticles
Yasukawa, Tomohiro,Kuremoto, Tatsuya,Miyamura, Hiroyuki,Kobayashi, Sh?
supporting information, p. 2716 - 2718 (2016/06/15)
Asymmetric arylation of aldimines catalyzed by heterogeneous chiral rhodium nanoparticles has been developed. The reaction proceeded in aqueous media without significant decomposition of the imines by hydrolysis to afford chiral (diarylmethyl)amines in high yields with outstanding enantioselectivities. This catalyst system exhibited the highest turnover number (700) in heterogeneous catalysts reported to date for these reactions. The reusability of the catalyst was also demonstrated.
Efficient metal-free photochemical borylation of aryl halides under batch and continuous-flow conditions
Chen, Kai,Zhang, Shuai,He, Pei,Li, Pengfei
, p. 3676 - 3680 (2016/06/09)
A rapid, chemoselective and metal-free C-B bond-forming reaction of aryl iodides and bromides in aqueous solution at low temperatures was discovered. This reaction is amenable to batch and continuous-flow conditions and shows exceptional functional group tolerance and broad substrate scope regarding both the aryl halide and the borylating reagent. Initial mechanistic experiments indicated a photolytically generated aryl radical as the key intermediate.
Fast and Tight Boronate Formation for Click Bioorthogonal Conjugation
Akgun, Burcin,Hall, Dennis G.
supporting information, p. 3909 - 3913 (2016/03/19)
A new click bioorthogonal reaction system was devised to enable the fast ligation (kON≈340 m-1 s-1) of conjugatable derivatives of a rigid cyclic diol (nopoldiol) and a carefully optimized boronic acid partner, 2-methyl-5-carboxymethylphenylboronic acid. Using NMR and fluorescence spectroscopy studies, the corresponding boronates were found to form reversibly within minutes at low micromolar concentration in water, providing submicromolar equilibrium constant (Keq≈105-106 m-1). Efficient protein conjugation under physiological conditions was demonstrated with model proteins thioredoxin and albumin, and characterized by mass spectrometry and gel electrophoresis.
