scholarly journals Structural Requirements of 1-(2-Pyridinyl)-5-pyrazolones for Disproportionation of Boronic Acids

Molecules ◽  
2021 ◽  
Vol 26 (22) ◽  
pp. 6814
Author(s):  
Joungmo Cho ◽  
Venkata Subbaiah Sadu ◽  
Yohan Han ◽  
Yunsoo Bae ◽  
Hwajeong Lee ◽  
...  
Keyword(s):  
Boronic Acid ◽  
Boronic Acids ◽  
Bidentate Ligand ◽  
Arylboronic Acid ◽  
Structural Requirements ◽  
Arylboronic Acids ◽  
Pyrazolone Derivatives ◽  
Unusual Formation

We observed an unusual formation of four-coordinate boron(III) complexes from the reaction of 1-(2-pyridinyl)-5-pyrazolone derivatives with arylboronic acids in the basic media. The exact mechanism is not clear; however, the use of unprotected boronic acid and the presence of a bidentate ligand appeared to be the key structural requirements for the transformation. The results suggest that base-promoted disproportionation of arylboronic acid with the assistance of the [N,O]-bidentate ligation of 1-(2-pyridinyl)-5-pyrazolone should take place and facilitate the formation of pyrazole diarylborinate. Experiments to obtain a deeper understanding of its mechanism are currently underway.

scholarly journals Catabolism of Arylboronic Acids by Arthrobacter nicotinovorans Strain PBA

2003 ◽  
Vol 69 (7) ◽  
pp. 4263-4267 ◽  
Author(s):  
Ana C. Negrete-Raymond ◽  
Barbara Weder ◽  
Lawrence P. Wackett
Keyword(s):  
Carbon Atom ◽  
Oxygen Atom ◽  
Boronic Acid ◽  
Phenylboronic Acid ◽  
Boronic Acids ◽  
Ring Carbon ◽  
Arylboronic Acids ◽  
Arthrobacter Nicotinovorans ◽  
Ring Carbon Atom

ABSTRACT Arthrobacter sp. strain PBA metabolized phenylboronic acid to phenol. The oxygen atom in phenol was shown to be derived from the atmosphere using 18O2. 1-Naphthalene-, 2-naphthalene-, 3-cyanophenyl-, 2,5-fluorophenyl-, and 3-thiophene-boronic acids were also transformed to monooxygenated products. The oxygen atom in the product was bonded to the ring carbon atom originally bearing the boronic acid substituent with all the substrates tested.

Rh(III)-Catalyzed Three-Component Syn-Carboamination of Alkenes Using Arylboronic Acids and Dioxazolones

2021 ◽  
Author(s):  
Sumin Lee ◽  
Tomislav Rovis
Keyword(s):  
Amino Acid ◽  
Boronic Acid ◽  
Boronic Acids ◽  
Reductive Elimination ◽  
Amino Acid Derivatives ◽  
Arylboronic Acids ◽  
Migratory Insertion ◽  
Series Of Experiments ◽  
By Products ◽  
Aryl Boronic Acid

<p>Herein we report a Rh(III)-catalyzed three-component carboamination of alkenes from readily available aryl boronic acids as a carbon source and dioxazolones as nitrogen electrophiles. This protocol provides facile access to valuable amine products including <i>a</i>-amino acid derivatives in good yield and excellent regioselectivity without the need for a directing functionality. A series of experiments suggest a mechanism in which the Rh(III) catalyst undergoes transmetalation with the aryl boronic acid followed by turnover limiting, alkene migratory insertion into the Rh(III)-aryl bond. Subsequently, fast Rh-nitrene formation provides the <i>syn</i>-carboamination product selectively after reductive elimination and proto-demetalation. Importantly, the protocol provides 3-component coupling products in preference to a variety of 2-component undesired by-products.</p>

scholarly journals Rh(III)-Catalyzed Three-Component Syn-Carboamination of Alkenes Using Arylboronic Acids and Dioxazolones

2021 ◽  
Author(s):  
Sumin Lee ◽  
Tomislav Rovis
Keyword(s):  
Amino Acid ◽  
Boronic Acid ◽  
Boronic Acids ◽  
Reductive Elimination ◽  
Amino Acid Derivatives ◽  
Arylboronic Acids ◽  
Migratory Insertion ◽  
Series Of Experiments ◽  
By Products ◽  
Aryl Boronic Acid

<p>Herein we report a Rh(III)-catalyzed three-component carboamination of alkenes from readily available aryl boronic acids as a carbon source and dioxazolones as nitrogen electrophiles. This protocol provides facile access to valuable amine products including <i>a</i>-amino acid derivatives in good yield and excellent regioselectivity without the need for a directing functionality. A series of experiments suggest a mechanism in which the Rh(III) catalyst undergoes transmetalation with the aryl boronic acid followed by turnover limiting, alkene migratory insertion into the Rh(III)-aryl bond. Subsequently, fast Rh-nitrene formation provides the <i>syn</i>-carboamination product selectively after reductive elimination and proto-demetalation. Importantly, the protocol provides 3-component coupling products in preference to a variety of 2-component undesired by-products.</p>

Arylboronic Acids in Self-condensation of Glucosamines Forming Deoxyfructosazine, Catalysts or Reagents?

2019 ◽  
Author(s):  
Meifeng Wang ◽  
Gan Zhu ◽  
Yiqun Li ◽  
Liuqun Gu
Keyword(s):  
Molecular Recognition ◽  
Boric Acid ◽  
Boronic Acid ◽  
Catalytic Mechanism ◽  
Organic Transformations ◽  
Food Industries ◽  
Arylboronic Acids ◽  
Excess Amount ◽  
Phenyl Boronic Acid ◽  
Boron Acid

Arylboronic acids were widely used as efficient catalysts in direct amide formation and other organic transformations. Surprisingly, reports on their use as catalysts in carbohydrates synthesis are very rare even though boron acid-diol complexation was extensively investigated in molecular recognition for saccharides and so on. Here we developed an efficient arylboronic acids catalyzed dimerization of glucosamines forming deoxyfructosazine which is important compound in pharmaceutical and food industries, against a commonly held belief that excess amount of phenyl boronic acid (or boric acid) is a must. A catalytic mechanism was also proposed and arylboronic acids instead of their boronates was identified as catalysts.

scholarly journals Practical iridium-catalyzed direct α-arylation of N-heteroarenes with (hetero)arylboronic acids by H2O-mediated H2 evolution

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Liang Cao ◽  
He Zhao ◽  
Rongqing Guan ◽  
Huanfeng Jiang ◽  
Pierre. H. Dixneuf ◽  
...  
Keyword(s):  
Structural Modification ◽  
Universal Access ◽  
Boronic Acids ◽  
Direct Access ◽  
Bidentate Ligands ◽  
H2 Evolution ◽  
Arylboronic Acids ◽  
Coupling Strategy ◽  
General Method ◽  
Operational Simplicity

AbstractDespite the widespread applications of 2-(hetero)aryl N-heteroarenes in numerous fields of science and technology, universal access to such compounds is hampered due to the lack of a general method for their synthesis. Herein, by a H2O-mediated H2-evolution cross-coupling strategy, we report an iridium(III)-catalyzed facile method to direct α-arylation of N-heteroarenes with both aryl and heteroaryl boronic acids, proceeding with broad substrate scope and excellent functional compatibility, oxidant and reductant-free conditions, operational simplicity, easy scalability, and no need for prefunctionalization of N-heteroarenes. This method is applicable for structural modification of biomedical molecules, and offers a practical route for direct access to 2-(hetero)aryl N-heteroarenes, a class of potential cyclometalated C^N ligands and N^N bidentate ligands that are difficult to prepare with the existing α-C-H arylation methods, thus filling an important gap in the capabilities of synthetic organic chemistry.

Palladium-catalysed cyclisation of ynamides and propargyl tethered iodosulfonamides with boronic acids leading to benzosultams

2021 ◽  
Author(s):  
K. Sandeep ◽  
Alla Siva Reddy ◽  
K. C. Kumara Swamy
Keyword(s):  
Boronic Acids ◽  
Arylboronic Acids ◽  
Synthetic Utility ◽  
Convenient Route

A convenient route to benzo[d]isothiazole and benzo[e][1,2]thiazine scaffolds using ynamides and arylboronic acids under [Pd]-catalysis is reported; the synthetic utility has been demonstrated by a gram-scale synthesis.

scholarly journals Efficient in situ N-heterocyclic carbene palladium(ii) generated from Pd(OAc)2 catalysts for carbonylative Suzuki coupling reactions of arylboronic acids with 2-bromopyridine under inert conditions leading to unsymmetrical arylpyridine ketones: synthesis, characterization and cytotoxic activities

RSC Advances ◽  
2018 ◽  
Vol 8 (70) ◽  
pp. 40000-40015 ◽  
Author(s):  
Nedra Touj ◽  
Abdullah S. Al-Ayed ◽  
Mathieu Sauthier ◽  
Lamjed Mansour ◽  
Abdel Halim Harrath ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Suzuki Coupling ◽  
Boronic Acids ◽  
Cytotoxic Activities ◽  
Coupling Reactions ◽  
Component System ◽  
Arylboronic Acids ◽  
Cross Coupling Reaction

The in situ prepared four component system Pd(OAc)2, 1,3-dialkylbenzimidazolium halides 2a–i and 4a–i, K2CO3 under CO atmosphere catalyses carbonylative cross-coupling reaction of 2-bromopyridine with various boronic acids to yield unsymmetrical arylpyridine ketones.

scholarly journals A Theoretical Model to Study the Interaction Between Boronic Acids and Insulin

2020 ◽  
Author(s):  
Durgesh Kumar ◽  
Kamlesh Kumari ◽  
PRASHANT SINGH
Keyword(s):  
Amino Acids ◽  
Theoretical Model ◽  
Boronic Acid ◽  
Significant Interaction ◽  
Biological Activities ◽  
Boronic Acids ◽  
Biological Molecules ◽  
Computational Tools ◽  
Medical Expertise ◽  
Stabilizing Agents

Boronic acids are widely used in various applications in view of their ability to recognize and bind at specific sites of the biological molecules to mimic several processes. Therefore, this has attracted the researchers, academician and medical expertise to explore them. In the present work, the authors have designed a theoretical approach to study the interaction of boronic acid with insulin using computational tools. A library of boronic acids (114 compounds) are designed, optimized and interacted with insulin using computational tools i.e. iGEMDOCK. Further, their different biological activities and toxicity are determined. Results indicates the promising potential of the boronic acids on interaction with the insulin. Amongst, 114 molecules of boronic acids, 3-Benzyloxyphenylboronic acid (71) showed the best interaction with amino-acids of insulin and significant interaction was shown with the Glu21 and His5 residues. Further, these results were compared with the stabilizing agents and found to be more potent.

Room temperature nickel-catalyzed cross-coupling of aryl-boronic acids with thiophenols: synthesis of diarylsulfides

2020 ◽  
Vol 18 (13) ◽  
pp. 2447-2458 ◽  
Author(s):  
Amit Bhowmik ◽  
Mahesh Yadav ◽  
Rodney A. Fernandes
Keyword(s):  
Room Temperature ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Arylboronic Acids

A mild and easy to operate NiCl2/2,2′-bipyridine-catalyzed cross-coupling of thiophenols with arylboronic acids has been developed for the synthesis of symmetric and unsymmetric diarylsulfides at room temperature and in air.

scholarly journals Cross coupling of benzylammonium salts with boronic acids using a well-defined N-heterocyclic carbene–palladium(ii) precatalyst

RSC Advances ◽  
2019 ◽  
Vol 9 (10) ◽  
pp. 5738-5741 ◽  
Author(s):  
Tao Wang ◽  
Jiarui Guo ◽  
Xiaojuan Wang ◽  
Han Guo ◽  
Dingli Jia ◽  
...  
Keyword(s):  
Bond Activation ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Arylboronic Acids

N-heterocyclic carbene–palladium(ii)-catalyzed cross-coupling of benzylammonium salts with arylboronic acids for the synthesis of diarylmethane derivatives via C–N bond activation has been developed.

Sign in / Sign up

Export Citation Format

Share Document