Trinuclear complexes of palladium(ii) with chalcogenated N-heterocyclic carbenes: catalysis of selective nitrile–primary amide interconversion and Sonogashira coupling

2017 ◽  
Vol 46 (38) ◽  
pp. 13065-13076 ◽  
Author(s):  
Pooja Dubey ◽  
Sonu Gupta ◽  
Ajai K. Singh
Keyword(s):  
Heterocyclic Carbenes ◽  
Sonogashira Coupling ◽  
Primary Amide ◽  
Trinuclear Complexes

The interconversion of nitriles to amides and Sonogashira coupling were catalyzed with Pd(ii) complexes (0.5–2 mol%).

Aryl-substituted Triarsiranes: Synthesis and Reactivity

2020 ◽  
Author(s):  
André Schumann ◽  
Jonas Bresien ◽  
Malte Fischer ◽  
Christian Hering-Junghans
Keyword(s):  
Organic Chemistry ◽  
Electronic Structure ◽  
Heterocyclic Carbenes ◽  
Synthetic Approaches ◽  
Inorganic And Organic

Cyclotriarsanes are rare and limited synthetic approaches have hampered reactivity studies on these systems. Described in here is a scalable synthetic protocol towards (AsAr)<sub>3</sub> (Ar = Dip, 2,6-<sup>i</sup>Pr<sub>2</sub>-C<sub>6</sub>H<sub>3</sub>; Tip, 2,4,6-<sup>i</sup>Pr<sub>3</sub>-C<sub>6</sub>H<sub>2</sub>), which allowed to study their reactivity towards [Cp<sub>2</sub>Ti(C<sub>2</sub>(SiMe<sub>3</sub>)<sub>2</sub>], affording titanocene diarsene complexes and towards N-heterocyclic carbenes (NHCs) to give straightforward access to a variety of NHC-arsinidene adducts. The electronic structure of the titanium diarsene complxes has been studied and they are best described as Ti(IV) species with a doubly reduced As<sub>2</sub>Ar<sub>2</sub> ligand. These findings will make (AsAr)<sub>3</sub> valuable precursors in the synthetic inorganic and organic chemistry.

Probing the Versatility of Shape-Persistent Tetraphenylmethane Dendrimers by Modification of the Skeleton

2019 ◽  
Author(s):  
Julio Ignacio Urzúa ◽  
Sandra Campana ◽  
Massimo Lazzari ◽  
Mercedes Torneiro
Keyword(s):  
Design Principle ◽  
Focal Point ◽  
Sonogashira Coupling ◽  
Terminal Alkyne ◽  
Double Phase ◽  
Rigid Rod ◽  
Convergent Approach ◽  
First And Second Generation ◽  
Oxidative Homocoupling ◽  
Hypercrosslinked Polymers

Tetraphenylmethane has emerged as a recurrent building block for advanced porous materials such as COFs, PAFs and hypercrosslinked polymers. Guided by a similar design principle, we have previously synthesized shape-persistent dendrimers with tetraphenylmethane nodes and ethynylene linkers. Here we report the generality of our approach by describing new dendritic architectures built from tetraphenylmethane. First, we prepared expanded dendrimers where the tetrahedral units are bonded through larger rigid rod spacers. Among the different synthetic strategies tested, the convergent route, with alternating steps of Pd-catalyzed Sonogashira coupling and alkyne activation by removal of TMS masking groups, efficiently afforded the first- and second-generation dendrimers. A second type of compounds having a linear diyne at the core is also described. The dendrimers of generations 1-2 were also synthesized by a convergent approach, with the diyne being assembled in the last step of the synthesis by a Glaser oxidative homocoupling of the corresponding dendrons bearing a terminal alkyne at the focal point. A third-generation dendrimer was also successfully prepared by a double-phase strategy.<br>

Application of Nitrogen Heterocyclic Carbenes in Organocatalysis

2020 ◽  
Vol 09 ◽  
Author(s):  
Minita Ojha ◽  
R. K. Bansal
Keyword(s):  
Asymmetric Catalysis ◽  
Building Blocks ◽  
Structural Features ◽  
Heterocyclic Carbenes ◽  
Stetter Reaction ◽  
Metal Pollutants ◽  
Synthetic Strategy ◽  
Wide Range ◽  
Benzoin Condensation ◽  
Nitrogen Heterocyclic

Background: During the last two decades, horizon of research in the field of Nitrogen Heterocyclic Carbenes (NHC) has widened remarkably. NHCs have emerged as ubiquitous species having applications in a broad range of fields, including organocatalysis and organometallic chemistry. The NHC-induced non-asymmetric catalysis has turned out to be a really fruitful area of research in recent years. Methods: By manipulating structural features and selecting appropriate substituent groups, it has been possible to control the kinetic and thermodynamic stability of a wide range of NHCs, which can be tolerant to a variety of functional groups and can be used under mild conditions. NHCs are produced by different methods, such as deprotonation of Nalkylhetrocyclic salt, transmetallation, decarboxylation and electrochemical reduction. Results: The NHCs have been used successfully as catalysts for a wide range of reactions making a large number of building blocks and other useful compounds accessible. Some of these reactions are: benzoin condensation, Stetter reaction, Michael reaction, esterification, activation of esters, activation of isocyanides, polymerization, different cycloaddition reactions, isomerization, etc. The present review includes all these examples published during the last 10 years, i.e. from 2010 till date. Conclusion: The NHCs have emerged as versatile and powerful organocatalysts in synthetic organic chemistry. They provide the synthetic strategy which does not burden the environment with metal pollutants and thus fit in the Green Chemistry.

New 2-Alkynyl Derivatives of the Acyclic Nucleoside 9-(2,3-Dihydroxypropyl)adenine and Their 6-Guanidinopurine Counterparts as Potential Effectors of Adenosine Receptors

2003 ◽  
Vol 68 (11) ◽  
pp. 2201-2218 ◽  
Author(s):  
Michal Česnek ◽  
Antonín Holý ◽  
Milena Masojídková
Keyword(s):  
Adenosine Receptors ◽  
Sonogashira Coupling ◽  
Acyclic Nucleoside ◽  
Derivatives Of

A series of the new 2-alkynyl derivatives of the acyclic nucleoside 9-(2,3-dihydroxypropyl)- adenine and their 6-guanidinopurine analogues were prepared by the Sonogashira coupling. The effect of the prepared compounds on A1 and A2A receptors was examined.

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