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• 852362-22-2 (1-benzyl-1H-pyrazol-4-yl)boronic acid 
• 108-90-7 chlorobenzene 
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• 16844-42-1 3-benzylsydnone 
• 536-74-3 phenylacetylene 
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• 50877-41-3 1-benzyl-4-bromo-1H-pyrazole 
• 2996-92-1 phenyl trimethylsiloxane 
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Relevant academic research and scientific papers

Synthesis of heteroleptic phosphine-copper(i) complexes: Fluorescence sensing and catalytic properties

Heteroleptic copper(i)-phosphine complexes have attracted considerable attention because of their diverse structures, and photophysical and catalytic properties. In this work, a series of heteroleptic diimine-diphosphine Cu(i) complexes (C1-C10) were synthesized quantitively using the designed bipyridine (L1-L4) and bidentate polyphosphine (L5-L8) as functional ligands. These mixed ligand-copper(i) complexes were fully characterized by 1H and 13C NMR spectroscopy, electrospray ionization mass spectrometry (ESI-MS) and elemental analysis. The detailed structures of complexes C1, C2, C5, C6, C9 and C10 were confirmed by single-crystal X-ray diffraction analysis. Moreover, these phosphine-Cu(i) complexes exhibited intense emissions either in the solid state or in solution under UV light excitation. The emissive complexes C1-C4 displayed highly sensitive luminescence sensing towards silver ions in a quenching fashion (turn-off). Furthermore, all the phosphine-protected copper(i) complexes exhibited high catalytic activity towards azide-alkyne cycloaddition (CuAAC) in water.

The Hiyama Cross-Coupling Reaction at Parts Per Million Levels of Pd: In Situ Formation of Highly Active Spirosilicates in Glycol Solvents

A palladium NNC-pincer complex at a 5 mol ppm loading efficiently catalyzed the Hiyama coupling reaction of aryl bromides with aryl(trialkoxy)silanes in propylene glycol to give the corresponding biaryls in excellent yields. This method was applied to the syntheses of adapalene and a biaryl-type liquid-crystalline compound, as well as to the derivatization of dextromethorphan and norfloxacin. ESI-MS and NMR analyses of the reaction mixture suggested the formation of pentacoordinate spirosilicate intermediates in situ. Preliminary theoretical studies revealed that the glycol-derived silicate intermediates formed in situ are quite reactive silicon reagents in the transmetalation step.

Ni: Vs. Pd in Suzuki-Miyaura sp2-sp2 cross-coupling: A head-to-head study in a comparable precatalyst/ligand system

The Suzuki-Miyaura reaction is a cornerstone method for sp2-sp2 cross-coupling in industry. There has been a concerted effort to enable the use of Ni catalysis as an alternative to Pd in order to mitigate cost and improve sustainability. Despite significant advances, ligand development for Ni-catalyzed Suzuki-Miyaura cross-coupling remains underdeveloped when compared to Pd and, as a consequence, ligands for Ni-catalyzed processes are typically taken from the Pd arena. In this study we evaluate the effect of using a similar Ni and Pd precatalyst based on a common bidentate ligand (dppf) in a head-to-head format for the most common type of biaryl couplings, establishing the practical implications of direct replacement of Pd with Ni, and identifying the potential origins of these observations in a mechanistic context.

Ecocatalyzed Suzuki cross coupling of heteroaryl compounds

A bio-based EcoPd was developed for the Suzuki cross coupling of heteroaryl compounds. Based on the ability of Eichhornia crassipes to bioconcentrate Pd in its roots, we addressed the transformation of plant-derived Pd metals to green catalysts. The methodology is based on eco-friendly procedures. It allowed the preparation of a wide range of heterocyclic biaryl and heterocyclic-heterocyclic biaryl compounds, with a low Pd catalyst loading. EcoPd was found to have the ideal microstructure to promote complex Suzuki reactions without ligands or additives. For the first time, post-reaction solution was treated by rhizofiltration. The resulting EcoPd has been reused with the same performance. This work has established the ecocatalysis concept as a powerful strategy for Pd sustainability, with the development of homogeneous catalysts that are easily recycled and reused.

Chemoselective Suzuki–Miyaura Cross-Coupling via Kinetic Transmetallation

Chemoselective Suzuki–Miyaura cross-coupling generally requires a designed deactivation of one nucleophile towards transmetallation. Here we show that boronic acids can be chemoselectively reacted in the presence of ostensibly equivalently reactive boronic acid pinacol (BPin) esters by kinetic discrimination during transmetallation. Simultaneous electrophile control allows sequential chemoselective cross-couplings in a single operation in the absence of protecting groups.

Cu-catalysed pyrazole synthesis in continuous flow

The synthesis of 1,4-disubstituted pyrazoles via the cycloaddition reaction of sydnones and terminal alkynes has been achieved employing silica-supported copper catalysts. Furthermore, this methodology has been successfully implemented in continuous flow

Pyrazole synthesis using a titanium-catalyzed multicomponent coupling reaction and synthesis of withasomnine

The titanium-catalyzed 3-component coupling of an alkyne, isonitrile, and amine can be used to generate tautomers of 1,3-diimines. These diimines produced in situ undergo cyclization with hydrazine and hydrazine derivatives in a one-pot procedure to provi

A versatile method for suzuki cross-coupling reactions of nitrogen heterocycles

(Chemical Equation Presented) A wide-ranging study of Suzuki reactions which use nitrogen-containing heterocycles is described (see scheme; dba = dibenzylideneacetone, Cy = cyclohexyl). This method is highly versatile (a single procedure was used for all substrates, including boronate esters and trifluoroborates), compatible with a variety of unprotected functionalities (e.g., NH2-and OH-substituted substrates), and efficient even with unactivated aryl chlorides.

A rationally designed universal catalyst for Suzuki-Miyaura coupling processes

Unprecedented scope, reactivity, and stability are displayed by a new catalyst system. This was demonstrated with general and efficient syntheses of sterically hindered (hetero)biaryls (see examples shown), mild coupling reactions of alkyl boron derivatives, and rapid coupling reactions of aryl chlorides at room temperature.