scholarly journals Recent Applications of Pd-Catalyzed Suzuki-Miyaura and Buchwald-Hartwig Couplings in Pharmaceutical Process Chemistry.

2021 ◽  
Author(s):  
Balaram S. Takale ◽  
Fan Yi Kong ◽  
Ruchita R. Thakore
Keyword(s):  
Drug Development ◽  
Large Scale ◽  
Cross Coupling ◽  
The Other ◽  
Coupling Reactions ◽  
Complex Molecules ◽  
Pharmaceutical Ingredients ◽  
The Core ◽  
Cross Coupling Reactions ◽  
Process Chemistry

Cross coupling reactions have changed the way complex molecules are synthesized. In particular, Suzuki-Miyaura and Buchwald-Hartwig amination reactions have given opportunities to elegantly make pharmaceutical ingredients. Indeed, these reactions are forefront at both the stages of drug development, medicinal chemistry, and process chemistry. On one hand, these reactions have given medicinal chemists a tool to derivatize the core molecule to arrive at scaffold rapidly. On the other hand, these cross couplings have offered the process chemists a smart tool to synthesize the development candidates safely, quickly, and efficiently. Generally, the application of cross coupling reactions is broad, and this review will specifically focus on their real (pharma) world applications in large scale synthesis those appeared in last two years.

scholarly journals Oxidative Photocatalytic Homo- and Cross-Coupling of Phenols: Non-Enzymatic, Catalytic Method for Coupling Tyrosine

2020 ◽  
Author(s):  
Kyle Niederer ◽  
Philip H. Gilmartin ◽  
Marisa Kozlowski
Keyword(s):  
High Selectivity ◽  
Cross Coupling ◽  
The Other ◽  
Nucleophilic Attack ◽  
Coupling Reactions ◽  
Catalytic Method ◽  
Cross Coupling Reactions ◽  
Oxidation Potentials ◽  
Coupling Partner ◽  
Radical Form

The first, oxidative photocatalytic method for phenol-phenol homo-coupling and cross-coupling is described and isolated yields of up to 97% are obtained. Measured oxidation potentials and computed nucleophilicity parameters are consistent with a nucleophilic attack of one partner onto the oxidized radical form of the other partner. Understanding of this model permitted development of cross-coupling reactions between nucleophilic phenols/arenes and easily oxidized phenols in high selectivity and efficiency. A highlight of this method is that one equivalent of each coupling partner is utilized. Building on these findings, the first non-enzymatic, catalytic method for coupling tyrosine was developed.

scholarly journals Oxidative Photocatalytic Homo- and Cross-Coupling of Phenols: Non-Enzymatic, Catalytic Method for Coupling Tyrosine

2020 ◽  
Author(s):  
Kyle Niederer ◽  
Philip H. Gilmartin ◽  
Marisa Kozlowski
Keyword(s):  
High Selectivity ◽  
Cross Coupling ◽  
The Other ◽  
Nucleophilic Attack ◽  
Coupling Reactions ◽  
Catalytic Method ◽  
Cross Coupling Reactions ◽  
Oxidation Potentials ◽  
Coupling Partner ◽  
Radical Form

The first, oxidative photocatalytic method for phenol-phenol homo-coupling and cross-coupling is described and isolated yields of up to 97% are obtained. Measured oxidation potentials and computed nucleophilicity parameters are consistent with a nucleophilic attack of one partner onto the oxidized radical form of the other partner. Understanding of this model permitted development of cross-coupling reactions between nucleophilic phenols/arenes and easily oxidized phenols in high selectivity and efficiency. A highlight of this method is that one equivalent of each coupling partner is utilized. Building on these findings, the first non-enzymatic, catalytic method for coupling tyrosine was developed.

Highly selective Suzuki reaction catalysed by a molecular Pd-P-MOF catalyst under mild conditions: role of ligands and palladium speciation

2022 ◽  
Author(s):  
Daniele Cartagenova ◽  
Stephan Bachmann ◽  
Kurt Püntener ◽  
Michelangelo Scalone ◽  
Mark A Newton ◽  
...  
Keyword(s):  
Large Scale ◽  
State Of The Art ◽  
Suzuki Reaction ◽  
Cross Coupling ◽  
Palladium Complexes ◽  
Fine Chemicals ◽  
Coupling Reactions ◽  
Mild Conditions ◽  
Cross Coupling Reactions

Cross-coupling reactions are a fundamental tool in the large scale synthesis of pharma-, agro- and fine chemicals. Homogeneous palladium complexes remain the state-of-the-art catalysts even though the use of heterogeneous...

A new approach to large scale production of dimethyl sulfone: a promising and strong recyclable solvent for ligand-free Cu-catalyzed C–C cross-coupling reactions

2020 ◽  
Vol 22 (6) ◽  
pp. 2069-2076
Author(s):  
Shen Cheng ◽  
Wei Wei ◽  
Xingyu Zhang ◽  
Hewei Yu ◽  
Mingming Huang ◽  
...  
Keyword(s):  
Dimethyl Sulfoxide ◽  
Large Scale ◽  
Cross Coupling ◽  
Scale Production ◽  
Coupling Reactions ◽  
New Approach ◽  
Dimethyl Sulfone ◽  
Cross Coupling Reactions ◽  
Large Scale Production ◽  
Ligand Free

Dimethyl sulfone (DMSN or MSM) was prepared via efficient oxidation of dimethyl sulfoxide and used and developed as an efficient, viscose, and recyclable solvent for ligand-free CuI-catalyzed Heck, Suzuki, and Sonogashira cross-coupling reactions.

An Overview of Solid Supported Palladium and Nickel Catalysts for C-C Cross Coupling Reactions

2020 ◽  
Vol 17 (5) ◽  
pp. 589-604
Author(s):  
Jaishri Chopra ◽  
Ajay K. Goswami ◽  
Prabhat K. Baroliya
Keyword(s):  
Large Scale ◽  
Supported Catalysts ◽  
Supported Catalyst ◽  
Cross Coupling ◽  
Nickel Catalysts ◽  
Coupling Reactions ◽  
Catalytic Systems ◽  
Heterogeneous Catalytic ◽  
Cross Coupling Reactions ◽  
Simple Filtration

Solid supported catalysts have been of considerable interest in organic synthesis for the last few years. Solid support provides an efficient heterogeneous catalytic system owing to facile recovery and extensive recycling by simple filtration because of possessing 3-R approach (Recoverable, Robust and Recyclable) and makes solid supported catalyst more appealing nowadays. In view of the high cost and shortage of furthermost used palladium catalyst, its recovery and recycling are vital issues for any large-scale application which are being overcome by using solid supported catalytic systems. Therefore, a variety of inorganic and organic solid-supported catalytic systems have been developed so far in order to address these challenges. This review attempts highlight a number of solid supported catalytic systems in the pro-active area of widely used C-C cross coupling reactions.

Synthesis of 2-Substituted 6-(Hydroxymethyl)purine Bases and Nucleosides

2005 ◽  
Vol 70 (10) ◽  
pp. 1669-1695 ◽  
Author(s):  
Peter Šilhár ◽  
Radek Pohl ◽  
Ivan Votruba ◽  
Michal Hocek
Keyword(s):  
Adenosine Deaminase ◽  
Cross Coupling ◽  
The Other ◽  
Coupling Reactions ◽  
Purine Derivatives ◽  
Cytostatic Effect ◽  
Purine Bases ◽  
Cross Coupling Reactions ◽  
Zinc Iodide

A facile and efficient methodology of the synthesis of 6-(hydroxymethyl)purine derivatives (bases and nucleosides) was developed based on Pd-catalyzed cross-coupling reactions of 6-halopurines or N-protected 2-amino-6-halopurines with (benzoyloxymethyl)zinc iodide followed by deprotection. Regioselective hydroxymethylations of 2,6-dihalopurines were also studied and used for the synthesis of 2-chloro-6-(hydroxymethyl)- or 2,6-bis(hydroxymethyl)purines. The 6-(hydroxymethyl)purine ribonucleoside 5f exerted high cytostatic effect and moderate inhibition of adenosine deaminase, while all the other derivatives were much less effective or entirely inactive.

scholarly journals Impact of Cross-Coupling Reactions in Drug Discovery and Development

Molecules ◽  
2020 ◽  
Vol 25 (15) ◽  
pp. 3493 ◽  
Author(s):  
Melissa J. Buskes ◽  
Maria-Jesus Blanco
Keyword(s):  
Drug Discovery ◽  
Large Scale ◽  
Critical Role ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Rapid Expansion ◽  
Coupling Reactions ◽  
Synthetic Process ◽  
Cross Coupling Reactions ◽  
The Impact

Cross-coupling reactions have played a critical role enabling the rapid expansion of structure–activity relationships (SAR) during the drug discovery phase to identify a clinical candidate and facilitate subsequent drug development processes. The reliability and flexibility of this methodology have attracted great interest in the pharmaceutical industry, becoming one of the most used approaches from Lead Generation to Lead Optimization. In this mini-review, we present an overview of cross-coupling reaction applications to medicinal chemistry efforts, in particular the Suzuki–Miyaura and Buchwald–Hartwig cross-coupling reactions as a remarkable resource for the generation of carbon–carbon and carbon–heteroatom bonds. To further appreciate the impact of this methodology, the authors discuss some recent examples of clinical candidates that utilize key cross-coupling reactions in their large-scale synthetic process. Looking into future opportunities, the authors highlight the versatility of the cross-coupling reactions towards new chemical modalities like DNA-encoded libraries (DELs), new generation of peptides and cyclopeptides, allosteric modulators, and proteolysis targeting chimera (PROTAC) approaches.

Oxidant-free oxidative gold catalysis: the new paradigm in cross-coupling reactions

2018 ◽  
Vol 54 (79) ◽  
pp. 11069-11083 ◽  
Author(s):  
Manjur O. Akram ◽  
Somsuvra Banerjee ◽  
Sagar S. Saswade ◽  
Vaibhav Bedi ◽  
Nitin T. Patil
Keyword(s):  
Cross Coupling ◽  
Gold Catalysis ◽  
Coupling Reactions ◽  
New Paradigm ◽  
Feature Article ◽  
The Core ◽  
Cross Coupling Reactions ◽  
Research Activities ◽  
Promising Area

The construction of C–C and C–X (X = hetero atom) bonds is the core aspect for the assembly of molecules. This feature article critically presents an overview of all the redox neutral cross-coupling reactions enabled by gold catalysis, which we believe would stimulate further research activities in this promising area.

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