73774-45-5Relevant articles and documents
Palladium-catalyzed B-diarylation of diethylaminoborane for the synthesis of diarylborinic acids
Igarashi, Takuya,Shimazumi, Ryoma,Tobisu, Mamoru
supporting information, p. 760 - 763 (2020/07/10)
The palladium-catalyzed synthesis of diarylborinic acid derivatives by intermolecular cross-coupling between aryl iodides and (amino)dihydrideborane is reported. The key to success of the reaction is the use of a less bulky diethylaminoborane reagent, which facilitates the second B-arylation.
BORON-CONTAINING SMALL MOLECULES FOR INHIBITING ACTIVITY OF A RECEPTOR-LIKE PROTEIN TYROSINE PHOSPHATASE
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Page/Page column 48-49, (2018/09/28)
A method is disclosed for altering the redox equilibrium of a transmembrane receptor-like protein tyrosine phosphatase (RPTP), particularly a type Ila RPTP, by chemically modulating the activity through contact of such an enzyme with a diaryl boron compou
Borinic Acids via Direct Arylation of Amine-Borane Complexes: An Air- and Water-Stable Boron Source
Richard, Jimmy,Birepinte, Mélodie,Charbonnier, Jean Baptiste,Liautard, Virginie,Pinet, Sandra,Pucheault, Mathieu
, p. 736 - 744 (2017/02/15)
A synthesis of borinic acids and borinates was optimized using amine-borane complexes as a water and air insensitive borylating agent. The reaction operates under convenient conditions using a non-cryogenic temperature and with no flash chromatography, and it gives no boron impurities. The reaction proceeds through a tandem dehydrogenation-double addition mechanism.
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.
Synthesis of Borinic Acids and Borinate Adducts Using Diisopropylaminoborane
Marciasini, Ludovic,Cacciuttolo, Bastien,Vaultier, Michel,Pucheault, Mathieu
, p. 3532 - 3535 (2015/07/28)
In situ formation of aryl Grignard under Barbier condition and diisopropylaminoborane as boron source allows a complete control of the addition onto the boron electrophile. Analytically pure borinic acid derivatives were produced at the gram scale without column chromatography and isolated as borinates adducts, with ethanolamine or 8-hydroxyquinoline, after workup.
METHOD FOR PREPARING BORINIC ACID DERIVATIVES AND NOVEL BORINIC ACID DERIVATIVES
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Paragraph 0125-0126, (2015/04/22)
The present invention relates to a method for preparing borinic acid derivatives and novel borinic acid derivatives. The preparing method of the present invention provides borinic acid derivatives of general formula (2): [in-line-formulae](Ar?2B(OH) ??(2)[/in-line-formulae] wherein Ar is the same as defined in the description and claims, selectively and in a high yield by reacting a compound of general formula (1): [in-line-formulae]Ar-M, ??(1)[/in-line-formulae] wherein Ar and M are the same as defined in the description and claims, with tri-t-butyl borate and then hydrolyzing the reaction product.
Design, synthesis and pharmacological characterization of analogs of 2-aminoethyl diphenylborinate (2-APB), a known store-operated calcium channel blocker, for inhibition of TRPV6-mediated calcium transport
Hofer, Alexandre,Kovacs, Gergely,Zappatini, Anna,Leuenberger, Michele,Hediger, Matthias A.,Lochner, Martin
, p. 3202 - 3213 (2013/07/11)
2-Aminoethyl diphenylborinate (2-APB) is a known modulator of the IP 3 receptor, the calcium ATPase SERCA, the calcium release-activated calcium channel Orai and TRP channels. More recently, it was shown that 2-APB is an efficient inhibitor of the epithelial calcium channel TRPV6 which is overexpressed in prostate cancer. We have conducted a structure-activity relationship study of 2-APB congeners to understand their inhibitory mode of action on TRPV6. Whereas modifying the aminoethyl moiety did not significantly change TRPV6 inhibition, substitution of the phenyl rings of 2-APB did. Our data show that the diaryl borinate moiety is required for biological activity and that the substitution pattern of the aryl rings can influence TRPV6 versus SOCE inhibition. We have also discovered that 2-APB is hydrolyzed and transesterified within minutes in solution.
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.
Mild and selective synthesis of an aryl boronic ester by equilibration of mixtures of boronic and borinic acid derivatives
Hawkins, Vanessa F.,Wilkinson, Mark C.,Whiting, Matthew
supporting information, p. 1265 - 1268 (2013/01/03)
Quenching of aryl Grignard reagents with 2-isopropoxy-4,4,5,5-tetramethyl- 1,3,2-dioxaborolane (isopropyl pinacol borate) under noncryogenic conditions can lead to mixtures of the corresponding boronic ester along with, generally undesired, borinic acid derivatives. We have found that in certain cases gentle heating of the crude reaction mixtures leads to complete equilibration to give the borinic esters as the sole product which can then be isolated in high yield. This novel equilibration can reduce the need for use of cryogenic conditions or large excesses of reagents to obtain selectivity during boronic ester syntheses.
Identification of borinic esters as inhibitors of bacterial cell growth and bacterial methyltransferases, CcrM and MenH
Benkovic, Stephen J.,Baker, Stephen J.,Alley,Woo, Youn-Hi,Zhang, Yong-Kang,Akama, Tsutomu,Mao, Weimin,Baboval, Justin,Rajagopalan, P. T. Ravi,Wall, Mark,Kahng, Lyn Sue,Tavassoli, Ali,Shapiro, Lucy
, p. 7468 - 7476 (2007/10/03)
As bacteria continue to develop resistance toward current antibiotics, we find ourselves in a continual battle to identify new antibacterial agents and targets. We report herein a class of boron-containing compounds termed borinic esters that have broad spectrum antibacterial activity with minimum inhibitory concentrations (MIC) in the low microgram/mL range. These compounds were identified by screening for inhibitors against Caulobacter crescentus CcrM, an essential DNA methyltransferase from Gram negative α-proteobacteria. In addition, we demonstrate that borinic esters inhibit menaquinone methyltransferase in Gram positive bacteria using a new biochemical assay for MenH from Bacillus subtilis. Our data demonstrate the potential for further development of borinic esters as antibacterial agents as well as leads to explore more specific inhibitors against two essential bacterial enzymes.
