scholarly journals Carbonylative Suzuki–Miyaura couplings of sterically hindered aryl halides: synthesis of 2-aroylbenzoate derivatives

2020 ◽  
Vol 18 (9) ◽  
pp. 1754-1759 ◽  
Author(s):  
Aya Ismael ◽  
Troels Skrydstrup ◽  
Annette Bayer
Keyword(s):  
Boronic Acid ◽  
Boronic Acids ◽  
Aryl Halides ◽  
Aryl Bromides ◽  
Sterically Hindered

A new protocol for carbonylative coupling of sterically hindered aryl bromides with boronic acids featuring slow addition of the boronic acid as a strategy to suppress unwanted non-carbonylative couplings for sterically hindered aryl bromides.

scholarly journals Cu(I)- and Pd(0)-Catalyzed Arylation of Oxadiamines with Fluorinated Halogenobenzenes: Comparison of Efficiency

Molecules ◽  
2020 ◽  
Vol 25 (5) ◽  
pp. 1084 ◽  
Author(s):  
Maria S. Lyakhovich ◽  
Alexei D. Averin ◽  
Olga K. Grigorova ◽  
Vitaly A. Roznyatovsky ◽  
Olga A. Maloshitskaya ◽  
...  
Keyword(s):  
Aryl Halides ◽  
Halogen Atoms ◽  
Aryl Iodides ◽  
Aryl Bromides ◽  
Sterically Hindered ◽  
Catalyzed Reactions

The comparison of the possibilities of Pd- and Cu-catalyzed amination reactions using fluorine-containing aryl bromides and iodides with oxadiamines to produce their N,N′-diaryl derivatives was carried out. The dependence of the reactivity of the aryl halides on the nature of the substituents and halogen atoms as well as on the structure of oxadiamines was investigated. It was found that the copper-catalyzed reactions were somewhat comparable with the palladium-mediated processes in the majority of cases, especially in the reactions with para-fluorine- and para-(trifluoromethyl)-substituted aryl halides, although the necessity to use aryl iodides in the Cu(I)-catalyzed amination was obvious. Pd catalysis was found inevitable for the successful amination of more sterically hindered ortho-(trifluoromethyl)aryl bromides.

Synthesis of a class of binaphthyl monophosphine ligands with a naphthofuran skeleton and their applications in Suzuki–Miyaura coupling reactions

2018 ◽  
Vol 42 (8) ◽  
pp. 5967-5971 ◽  
Author(s):  
Zihong Zhou ◽  
Hao Liang ◽  
Wang Xia ◽  
Huixuan Chen ◽  
Yaqi Zhang ◽  
...  
Keyword(s):  
Boronic Acids ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Excellent Activity ◽  
Sterically Hindered

L6–Pd2(dba)3 showed excellent activity in the Suzuki–Miyaura reaction of sterically hindered and electron-rich aryl halides with aryl boronic acids.

scholarly journals The catalytic mechanism of the Suzuki-Miyaura reaction

2021 ◽  
Author(s):  
Juliet macharia ◽  
Chetan Joshi ◽  
Joseph Izzo ◽  
Victor Wambua ◽  
Sungjin Kim ◽  
...  
Keyword(s):  
Catalytic Mechanism ◽  
Palladium Complex ◽  
Isotope Effects ◽  
Oxidative Addition ◽  
Kinetic Isotope Effects ◽  
Boronic Acids ◽  
Aryl Halides ◽  
Kinetic Isotope ◽  
Aryl Bromides ◽  
Insight Into

Abstract: Experimental and theoretical 13C kinetic isotope effects are utilized to obtain atomistic insight into the catalytic mechanism of the Pd(PPh3)4 catalyzed Suzuki-Miyaura reaction of aryl halides and aryl boronic acids. Under catalytic conditions, we establish that oxidative addition of aryl bromides occurs to a 12-electron monoligated palladium complex (Pd(PPh3)). For aryl iodides, the first irreversible step in the catalytic cycle precedes oxidative addition and is shown to be binding of the iodoarene to Pd(PPh3). Our results suggest that the commonly proposed oxidative addition to the 14-electron Pd(PPh3)2 complex can occur only in the presence of excess added ligand or under stoichiometric conditions. The transmetalation step, under catalytic conditions, is shown to proceed via a tetracoordinate boronate (8B4) intermediate with a Pd-O-B linkage.

An efficient indenyl-derived phosphine ligand for the Suzuki–Miyaura coupling of sterically hindered aryl halides

2016 ◽  
Vol 14 (20) ◽  
pp. 4664-4668 ◽  
Author(s):  
Yan Liu ◽  
Hui Peng ◽  
Jia Yuan ◽  
Meng-Qi Yan ◽  
Xue Luo ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Phosphine Ligand ◽  
Aryl Halides ◽  
Efficient Catalyst ◽  
Highly Efficient ◽  
Cross Coupling Reaction ◽  
Sterically Hindered

An air-stable aryl substituted indenyl phosphine used in combination with Pd(OAc)2 provides a highly efficient catalyst for the Suzuki–Miyaura cross-coupling reaction of sterically hindered aryl halides with aryl boronic acids.

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.

scholarly journals Amine-Catalysed Suzuki–Miyaura-Type Coupling? the Identification and Isolation of the Palladium Culprits.

2021 ◽  
Author(s):  
Mickaël Avanthay ◽  
Robin Bedford ◽  
Callum Begg ◽  
Dietrich Böse ◽  
Jonathan Clayden ◽  
...  
Keyword(s):  
Catalytic Activity ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Palladium Complexes ◽  
Aryl Halides ◽  
Type Coupling ◽  
Paradigm Shifting

A recent report in Nature Catalysis detailed the potentially paradigm-shifting organocatalysis of Suzuki cross-coupling of aryl halides with aryl boronic acids, catalysed by simple amine species. We have conducted a reinvestigation of key claims in this paper across multiple academic and industrial laboratories that shows that the observed catalytic activity cannot be due to the amine, but rather is due to tricyclohexylphosphine palladium complexes that are readily entrained during the purification of the amine<b>.</b>

Silver catalyzed C–C and C–S coupling of aryl halides and thiols with boronic acids

2012 ◽  
Vol 53 (52) ◽  
pp. 7023-7027 ◽  
Author(s):  
Rima Das ◽  
Debashis Chakraborty
Keyword(s):  
Boronic Acids ◽  
Aryl Halides
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