scholarly journals Synthesis and electronic properties of nitrogen-doped π-extended polycyclic aromatic dicarboximides with multiple redox processes

2021 ◽  
Author(s):  
Matías J. Alonso-Navarro ◽  
Alexandra Harbuzaru ◽  
Marcos Martínez-Fernández ◽  
Paula Pérez Camero ◽  
Juan Teodomiro Lopez Navarrete ◽  
...  
Keyword(s):  
Electronic Properties ◽  
Cross Coupling ◽  
Redox Processes ◽  
Coupling Reactions ◽  
Nitrogen Doped ◽  
Cross Coupling Reactions ◽  
Synthetic Procedure ◽  
Polycyclic Aromatic

In this work, a series of nitrogen-doped polycyclic aromatic mono and dicarboximides was designed, and their synthesis is reported by an innovative synthetic procedure that avoids metal-based cross-coupling reactions. A...

Protocol for Palladium/N-Heterocyclic Carbene-Catalyzed Suzuki–Miyaura Cross-Coupling of Amides by N–C(O) Activation

Synthesis ◽  
2020 ◽  
Author(s):  
Peng Lei ◽  
Guangchen Li ◽  
Michal Szostak ◽  
Yun Ling ◽  
Jie An ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
Room Temperature ◽  
Bond Activation ◽  
Process Development ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Amide Bonds ◽  
Cross Coupling Reactions ◽  
Synthetic Procedure ◽  
Operational Simplicity

AbstractAmides are among the most important and ubiquitous functional groups in organic chemistry and process development. In this Practical Synthetic Procedure, a protocol for the Suzuki–Miyaura cross-coupling of amides by selective N–C(O) bond activation catalyzed by commercially available, air- and moisture-stable palladium/N-heterocyclic carbene (NHC) complexes is described. The procedure described involves [Pd(IPr)(cin)Cl] [IPr = 2,6-(diisopropylphenyl)imidazol-2-ylidene, cin = cinnamyl] at 0.10 mol% at room temperature and is performed on decagram scale. Furthermore, a procedure for the synthesis of amide starting materials is accomplished via selective N-tert-butoxycarbonylation, which is the preferred method over N-acylation. The present protocol carries advantages of operational simplicity, commercial availability of catalysts, and excellent conversions at low catalyst loadings. The method is generally useful for activation of N–C(O) amide bonds in a broad spectrum of amide precursors. The protocol should facilitate the implementation of amide cross-coupling reactions.

Mesoporous nitrogen-doped carbon for copper-mediated Ullmann-type C–O/–N/–S cross-coupling reactions

RSC Advances ◽  
2013 ◽  
Vol 3 (6) ◽  
pp. 1890-1895 ◽  
Author(s):  
Pengfei Zhang ◽  
Jiayin Yuan ◽  
Haoran Li ◽  
Xiaofeng Liu ◽  
Xuan Xu ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Nitrogen Doped ◽  
Cross Coupling Reactions ◽  
Type C ◽  
Nitrogen Doped Carbon

Functionalized aromatics aligned with the three Cartesian axes: Extension of centropolyindane chemistry

2006 ◽  
Vol 78 (4) ◽  
pp. 749-775 ◽  
Author(s):  
Dietmar Kuck
Keyword(s):  
Aromatic Hydrocarbons ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
X Ray ◽  
Cartesian Space ◽  
Cross Coupling Reactions ◽  
Geometrical Features ◽  
The Family ◽  
Polycyclic Aromatic ◽  
First Time

The unique geometrical features and structural potential of the centropolyindanes, a complete family of novel, 3D polycyclic aromatic hydrocarbons, are discussed with respect to the inherent orthogonality of their arene units. Thus, the largest member of the family, centrohexaindane, a topologically nonplanar hydrocarbon, is presented as a "Cartesian hexabenzene", because each of its six benzene units is stretched into one of the six directions of the Cartesian space. This feature is discussed on the basis of the X-ray crystal structures of centrohexaindane and two lower members of the centropolyindane family, viz. the parent tribenzotriquinacenes. Recent progress in multiple functionalization and extension of the indane wings of selected centropolyindanes is reported, including several highly efficient six- and eight-fold C-C cross-coupling reactions. Some particular centropolyindane derivatives are presented, such as the first twelve-fold functionalized centrohexaindane and a tribenzotriquinacene bearing three mutually orthogonal phenanthroline groupings at its molecular periphery. Challenges to further extend the arene peripheries of the tribenzotriquinacenes and fenestrindanes to give, eventually, graphite cuttings bearing a central bowl- or saddle-shaped center are outlined, as is the hypothetical generation of a "giant" nanocube consisting of eight covalently bound tribenzotriquinacene units. Along these lines, our recent discovery of a related, solid-state supramolecular cube, containing eight molecules of a particular tribromotrinitrotribenzotriquinacene of the same absolute configuration, is presented for the first time.

New interesting molecular topologies by way of modern cross-coupling reactions

2006 ◽  
Vol 78 (4) ◽  
pp. 813-830 ◽  
Author(s):  
Armin de Meijere ◽  
Baldur Stulgies ◽  
Karsten Albrecht ◽  
Karsten Rauch ◽  
Hermann A. Wegner ◽  
...  
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Transition Metal ◽  
Aromatic Hydrocarbons ◽  
Cross Coupling ◽  
Spectroscopic Properties ◽  
Coupling Reactions ◽  
Highly Efficient ◽  
Cross Coupling Reactions ◽  
Polycyclic Aromatic ◽  
Metal Catalyzed

Modern transition-metal-catalyzed cross-coupling reactions, especially of the Kumada, Heck, and Suzuki types, have provided facile access to various bridge-annelated [2.2]paracyclophane derivatives including trifoliaphane and its tribenzo analog. The reduction of trifoliaphane with potassium metal in [D8]-THF led to hexakis[p-benzyl]benzene anion, which could efficiently be trapped with various electrophiles. Highly efficient multifold Suzuki couplings were performed with hexabromobenzene, octabromonaphthalene, and hexabromotriphenylene. The obtained hexa- and octaalkenylarene derivatives disclose interesting molecular shapes. Eventually, a newly developed cascade coupling of bromoarenes containing peri-positioned C-H bonds has led to indeno-annelated polycyclic aromatic hydrocarbons including indenocorannulene as well as the tetrakis- and tris(tert-butylindeno)pyrene which disclose very interesting spectroscopic properties. In particular, tetrakis(tert-butylindeno)pyrene self-assembles in solution by way of π-stacking, and it can be reduced with potassium metal to a stable dianion, a readily dimerizing trianion radical, and a tetraanion.

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