scholarly journals Decarboxylative cross-coupling reactions for P(O)–C bond formation

RSC Advances ◽  
2018 ◽  
Vol 8 (46) ◽  
pp. 26383-26398 ◽  
Author(s):  
Akram Hosseinian ◽  
Fatemeh Alsadat Hosseini Nasab ◽  
Sheida Ahmadi ◽  
Zahra Rahmani ◽  
Esmail Vessally
Keyword(s):  
Organic Chemistry ◽  
Organic Compounds ◽  
Medicinal Chemistry ◽  
Bond Formation ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Materials Chemistry ◽  
Cross Coupling Reactions ◽  
Agricultural Chemistry ◽  
Phosphorus Containing

Phosphorus-containing compounds are one of the most important classes of organic compounds, which have wide applications in organic chemistry, medicinal chemistry, agricultural chemistry, and materials chemistry.

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>

Withdrawal Notice: Recent Advances in Sonogashira Cross-Coupling Reactions Under Solvent-Free Conditions

2020 ◽  
Vol 24 ◽  
Author(s):  
Teng Wang ◽  
Zongrui Liu ◽  
Songlin Wang ◽  
Esmail Vessally
Keyword(s):  
Organic Chemistry ◽  
Editorial Policy ◽  
Cross Coupling ◽  
Solvent Free ◽  
Coupling Reactions ◽  
Editorial Policies ◽  
Cross Coupling Reactions ◽  
Recent Advances ◽  
Solvent Free Conditions ◽  
Copyright Permission

The article has been withdrawn at the request of editor of the journal Current Organic Chemistry: Bentham Science apologizes to the readers of the journal for any inconvenience this may have caused. The Bentham Editorial Policy on Article Withdrawal can be found at https://benthamscience.com/editorial-policies-main.php BENTHAM SCIENCE DISCLAIMER: It is a condition of publication that manuscripts submitted to this journal have not been published and will not be simultaneously submitted or published elsewhere. Furthermore, any data, illustration, structure or table that has been published elsewhere must be reported, and copyright permission for reproduction must be obtained. Plagiarism is strictly forbidden, and by submitting the article for publication the authors agree that the publishers have the legal right to take appropriate action against the authors, if plagiarism or fabricated information is discovered. By submitting a manuscript, the authors agree that the copyright of their article is transferred to the publishers if and when the article is accepted for publication.

scholarly journals Convenient Access to Functionalized Non-Symmetrical Atropisomeric 4,4′-Bipyridines

Compounds ◽  
2021 ◽  
Vol 1 (2) ◽  
pp. 58-74
Author(s):  
Emmanuel Aubert ◽  
Emmanuel Wenger ◽  
Paola Peluso ◽  
Victor Mamane
Keyword(s):  
Solid State ◽  
Intermolecular Interactions ◽  
Medicinal Chemistry ◽  
Crystal Packing ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Halogen Bonds ◽  
Cross Coupling Reactions ◽  
Cyano Groups ◽  
Post Functionalization

Non-symmetrical chiral 4,4′-bipyridines have recently found interest in organocatalysis and medicinal chemistry. In this regard, the development of efficient methods for their synthesis is highly desirable. Herein, a series of non-symmetrical atropisomeric polyhalogenated 4,4′-bipyridines were prepared and further functionalized by using cross-coupling reactions. The desymmetrization step is based on the N-oxidation of one of the two pyridine rings of the 4,4′-bipyridine skeleton. The main advantage of this methodology is the possible post-functionalization of the pyridine N-oxide, allowing selective introduction of chlorine, bromine or cyano groups in 2- and 2′-postions of the chiral atropisomeric 4,4′-bipyridines. The crystal packing in the solid state of some newly prepared derivatives was analyzed and revealed the importance of halogen bonds in intermolecular interactions.

Copper-catalyzed cross-coupling reactions for C–P bond formation

RSC Advances ◽  
2015 ◽  
Vol 5 (65) ◽  
pp. 52824-52831 ◽  
Author(s):  
Hui Zhang ◽  
Xue-Yan Zhang ◽  
Dao-Qing Dong ◽  
Zu-Li Wang
Keyword(s):  
Bond Formation ◽  
Cross Coupling ◽  
Phosphorus Compounds ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

Phosphorus compounds are important compounds in many areas.

scholarly journals Computational Insights into Intramolecular Cross-Coupling of Quaternary Borate Salts

2021 ◽  
Author(s):  
Florian Matz ◽  
Arif Music ◽  
Dorian Didier ◽  
Thomas C. Jagau
Keyword(s):  
Organic Synthesis ◽  
Energy Barrier ◽  
Density Functional ◽  
Bond Formation ◽  
Cross Coupling ◽  
Coupled Cluster ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Product Distributions ◽  
Borate Salts

Cross-coupling reactions for C-C bond formation represent a cornerstone of organic synthesis. In most cases, they make use of transition metals, which has several downsides. Recently, metal-free alternatives relying on electrochemistry have gained interest. One example of such a reaction is the oxidation of tetraorganoborate salts that initiates aryl-aryl and aryl-alkenyl couplings with promising selectivities. This work investigates the mechanism of this reaction computationally using density functional and coupled-cluster theory. Our calculations reveal a distinct difference between aryl-alkenyl and aryl-aryl couplings: While C-C bond formation occurs irreversibly and without an energy barrier if an alkenyl residue is involved, many intermediates can be identified in aryl-aryl couplings. In the latter case, intramolecular transitions between reaction paths leading to different products are possible. Based on the energy differences between these intermediates, we develop a kinetic model to estimate product distributions for aryl-aryl couplings.<br>

scholarly journals Computational Insights into Intramolecular Cross-Coupling of Quaternary Borate Salts

2021 ◽  
Author(s):  
Florian Matz ◽  
Arif Music ◽  
Dorian Didier ◽  
Thomas C. Jagau
Keyword(s):  
Organic Synthesis ◽  
Energy Barrier ◽  
Density Functional ◽  
Bond Formation ◽  
Cross Coupling ◽  
Coupled Cluster ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Product Distributions ◽  
Borate Salts

Cross-coupling reactions for C-C bond formation represent a cornerstone of organic synthesis. In most cases, they make use of transition metals, which has several downsides. Recently, metal-free alternatives relying on electrochemistry have gained interest. One example of such a reaction is the oxidation of tetraorganoborate salts that initiates aryl-aryl and aryl-alkenyl couplings with promising selectivities. This work investigates the mechanism of this reaction computationally using density functional and coupled-cluster theory. Our calculations reveal a distinct difference between aryl-alkenyl and aryl-aryl couplings: While C-C bond formation occurs irreversibly and without an energy barrier if an alkenyl residue is involved, many intermediates can be identified in aryl-aryl couplings. In the latter case, intramolecular transitions between reaction paths leading to different products are possible. Based on the energy differences between these intermediates, we develop a kinetic model to estimate product distributions for aryl-aryl couplings.<br>

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