73774-44-4Relevant academic research and scientific papers
Borinic acid catalysed peptide synthesis
El Dine, Tharwat Mohy,Rouden, Jacques,Blanchet, Jér?me
supporting information, p. 16084 - 16087 (2015/11/10)
The catalytic synthesis of peptides is a major challenge in the modern organic chemistry hindered by the well-established use of stoichiometric coupling reagents. Herein, we describe for the first time that borinic acid is able to catalyse this reaction under mild conditions with an improved activity compared to our recently developed thiophene-based boronic acid. This catalyst is particularly efficient for peptide bond synthesis affording dipeptides in good yields without detectable racemization.
Cross-coupling of diarylborinic acids and anhydrides with arylhalides catalyzed by a phosphite/N-heterocyclic carbene co-supported palladium catalyst system
Chen, Xiaofeng,Ke, Haihua,Chen, Yao,Guan, Changwei,Zou, Gang
, p. 7572 - 7578 (2012/10/29)
A highly efficient cross-coupling of diarylborinic acids and anhydrides with aryl chlorides and bromides has been effected by using a palladium catalyst system co-supported by a strong σ-donor N-heterocyclic carbene (NHC), N,N′-bis(2,6-diisopropylphenyl) imidazol-2-ylidene, and a strong π-acceptor phosphite, triphenylphosphite, in tert-BuOH in the present of K3PO4·3H2O. Unsymmetrical biaryls with a variety of functional groups could be obtained in good to excellent yields using as low as 0.01, 0.2-0.5, and 1 mol % palladium loadings for aryl bromides and activated and deactivated aryl chlorides, respectively, under mild conditions. A ligand synergy between the σ-donor NHC and the π-acceptor phosphite in the Pd/NHC/P(OPh)3 catalytic system has been proposed to be responsible for the high efficacy to arylchlorides in the cross-coupling. A scalable and economical process has therefore been developed for synthesis of Sartan biphenyl from the Pd/NHC/P(OPh)3 catalyzed cross-coupling of di(4-methylphenyl)borinic acid with 2-chlorobenzonitrile.
Palladium-catalyzed cross-coupling reaction of potassium diaryldifluoroborates with aryl halides
Ito, Takatoshi,Iwai, Toshiyuki,Mizuno, Takumi,Ishino, Yoshio
, p. 1435 - 1438 (2007/10/03)
The catalytic cross-coupling reaction of potassium diaryldifluoroborates with aryl halides proceeds to afford the biphenyls in good yields. These salts on an arylation reagent were readily prepared via a protocol of the Grignard method and transformation to potassium salts. Two aryl groups of these salts were efficiently transferred in the Suzuki-Miyaura reaction.
