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.

Cross-coupling reactions with esters, aldehydes, and alcohols

2021 ◽  
Author(s):  
Yan-Long Zheng ◽  
Stephen G. Newman
Keyword(s):  
Functional Groups ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Feature Article ◽  
Cross Coupling Reactions

This feature article describes how diverse oxygen-containing functional groups such as esters, aldehydes, and alcohols can participate in cross-coupling reactions to prepare amides, ketones, alcohols, and beyond.

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 Concise, Gram-Scale Synthesis of Furo[2,3-B]pyridines, with Functional Handles for Chemoselective Cross-Coupling

2020 ◽  
Author(s):  
Sean O'Byrne ◽  
Benjamin J. Eduful ◽  
Timothy M. Willson ◽  
David Drewry
Keyword(s):  
Cross Coupling ◽  
Scaling Up ◽  
Easy Access ◽  
Coupling Reactions ◽  
Synthetic Route ◽  
The Core ◽  
Cross Coupling Reactions ◽  
Sar Studies ◽  
Structure Activity ◽  
One Step

<p>A concise 4-step synthesis of furo[2,3-b]pyridines, with handles in the 3 and 5 positions for palladium mediated cross-coupling reactions, is described. The synthetic route has been optimized, with only one step requiring purification by column chromatography. The route is amenable to scaling-up and was successfully executed on a multi-gram scale. Furopyridines are of growing interest in medicinal chemistry, and this route should enable easy access to the core for structure-activity relationship (SAR) studies.</p>

scholarly journals Concise, Gram-Scale Synthesis of Furo[2,3-B]pyridines, with Functional Handles for Chemoselective Cross-Coupling

2020 ◽  
Author(s):  
Sean O'Byrne ◽  
Benjamin J. Eduful ◽  
Timothy M. Willson ◽  
David Drewry
Keyword(s):  
Cross Coupling ◽  
Scaling Up ◽  
Easy Access ◽  
Coupling Reactions ◽  
Synthetic Route ◽  
The Core ◽  
Cross Coupling Reactions ◽  
Sar Studies ◽  
Structure Activity ◽  
One Step

<p>A concise 4-step synthesis of furo[2,3-b]pyridines, with handles in the 3 and 5 positions for palladium mediated cross-coupling reactions, is described. The synthetic route has been optimized, with only one step requiring purification by column chromatography. The route is amenable to scaling-up and was successfully executed on a multi-gram scale. Furopyridines are of growing interest in medicinal chemistry, and this route should enable easy access to the core for structure-activity relationship (SAR) studies.</p>

Dual Nickel/Palladium-Catalyzed Reductive Cross-Coupling Reactions Between Two Phenol Derivatives

2020 ◽  
Author(s):  
Baojian Xiong ◽  
Yue Li ◽  
Yin Wei ◽  
Søren Kramer ◽  
Zhong Lian
Keyword(s):  
Functional Group ◽  
Low Cost ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Phenol Derivatives ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
One Step ◽  
Aryl Tosylates ◽  
Low Sensitivity

Cross-coupling between substrates that can be easily derived from phenols is highly attractive due to the abundance and low cost of phenols. Here, we report a dual nickel/palladium-catalyzed reductive cross-coupling between aryl tosylates and aryl triflates; both substrates can be accessed in just one step from readily available phenols. The reaction has a broad functional group tolerance and substrate scope (>60 examples). Furthermore, it displays low sensitivity to steric effects demonstrated by the synthesis of a 2,2’disubstituted biaryl and a fully substituted aryl product. The widespread presence of phenols in natural products and pharmaceuticals allow for straightforward late-stage functionalization, illustrated with examples such as Ezetimibe and tyrosine. NMR spectroscopy and DFT calculations indicate that the nickel catalyst is responsible for activating the aryl triflate, while the palladium catalyst preferentially reacts with the aryl tosylate.

An Iron-Based Catalyst Enables The Enantioconvergent Synthesis of Chiral 1,1-Diarylalkanes Through a Suzuki-Miyaura Cross-Coupling Reaction

2020 ◽  
Author(s):  
Chet Tyrol ◽  
Nang Yone ◽  
Connor Gallin ◽  
Jeffery Byers
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Radical Intermediates ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Boronic Esters ◽  
Carbon Centered Radical ◽  
Iron Based ◽  
High Yields

By using an iron-based catalyst, access to enantioenriched 1,1-diarylakanes was enabled through an enantioselective Suzuki-Miyaura crosscoupling reaction. The combination of a chiral cyanobis(oxazoline) ligand framework and 1,3,5-trimethoxybenzene additive were essential to afford high yields and enantioselectivities in cross-coupling reactions between unactivated aryl boronic esters and a variety of benzylic chlorides, including challenging ortho-substituted benzylic chloride substrates. Mechanistic investigations implicate a stereoconvergent pathway involving carbon-centered radical intermediates.

Phosphino-Triazole Ligands for Palladium-Catalysed Cross-Coupling

2018 ◽  
Author(s):  
Yiming Zhao ◽  
Huy van Nguyen ◽  
Louise Male ◽  
Philip Craven ◽  
Benjamin R. Buckley ◽  
...  
Keyword(s):  
Drug Discovery ◽  
Cross Coupling ◽  
Product Formation ◽  
Coupling Reactions ◽  
Volume Determination ◽  
Online Tool ◽  
Triazole Derivatives ◽  
Cross Coupling Reactions ◽  
Modelling Approaches

<div>Twelve 1,5-disubtituted and fourteen 5-substituted 1,2,3-triazole derivatives bearing diaryl or dialkyl phosphines at the 5-position were synthesised and used as ligands for palladium-catalysed Suzuki-Miyaura cross-coupling reactions. Bulky substrates were tested, and lead-like product formation was demonstrated. The online tool SambVca 2.0 was used to assess steric parameters of ligands and preliminary buried volume determination using XRD obtained data in a small number of cases proved to be informative. Two modelling approaches were compared for the determination of</div><div>the buried volume of ligands where XRD data was not available. An approach with imposed steric restrictions was found to be superior in leading to buried volume determinations that closely correlate with observed reaction conversions. The online tool LLAMA was used to determine lead-likeness of potential Suzuki-Miyaura cross-coupling products, from which ten of the most lead-like were successfully synthesised. Thus, confirming these readily accessible triazole-containing phosphines as highly suitable ligands for reaction screening and optimisation in drug discovery campaigns.</div>

A Revised Modular Approach to D8-THC and Derivatives Through Late-Stage Suzuki-Miyaura Cross-Coupling Reactions

2019 ◽  
Author(s):  
Victor Bloemendal ◽  
Floris P. J. T. Rutjes ◽  
Thomas J. Boltje ◽  
Daan Sondag ◽  
Hidde Elferink ◽  
...  
Keyword(s):  
Biological Activity ◽  
Late Stage ◽  
Medicinal Chemistry ◽  
Cross Coupling ◽  
Modular Approach ◽  
Coupling Reactions ◽  
One Pot ◽  
Biologically Relevant ◽  
Cross Coupling Reactions ◽  
Chemistry Research

<p>In this manuscript we describe a modular pathway to synthesize biologically relevant (–)-<i>trans</i>-Δ<sup>8</sup>-THC derivatives, which can be used to modulate the pharmacologically important CB<sub>1</sub> and CB<sub>2</sub> receptors. This pathway involves a one-pot Friedel-Crafts alkylation/cyclization protocol, followed by Suzuki-Miyaura cross-coupling reactions and gives rise to a series of new Δ<sup>8</sup>-THC derivatives. In addition, we demonstrate using extensive NMR evidence that similar halide-substituted Friedel-Crafts alkylation/cyclization products in previous articles were wrongly assigned as the para-isomers, which also has consequence for the assignment of the subsequent cross-coupled products and interpretation of their biological activity. </p> <p>Considering the importance of the availability of THC derivatives in medicinal chemistry research and the fact that previously synthesized compounds were wrongly assigned, we feel this research is describing a straightforward pathway into new cannabinoids.</p>

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