Copper-catalyzed C(sp2)-C(sp) Sonogashira-type cross-coupling reactions accelerated by polycyclic aromatic hydrocarbons

2015 ◽  
Vol 29 (6) ◽  
pp. 353-356 ◽  
Author(s):  
Wei Xu ◽  
Bo Yu ◽  
Huaming Sun ◽  
Guofang Zhang ◽  
Weiqiang Zhang ◽  
...  
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Aromatic Hydrocarbons ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Polycyclic Aromatic

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.

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.

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...

scholarly journals Access tetracoordinate boron-doped polycyclic aromatic hydrocarbons with aggregation-induced emission under mild conditions

2021 ◽  
Author(s):  
Long Jiang ◽  
Dehui Tan ◽  
Xiaobin Chen ◽  
Tinghao Ma ◽  
Baoliang Zhang ◽  
...  
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Functional Groups ◽  
Aromatic Hydrocarbons ◽  
Coupling Reactions ◽  
Optoelectronic Materials ◽  
Aggregation Induced Emission ◽  
Boron Doped ◽  
Polycyclic Aromatic ◽  
The Difference ◽  
Oxidative Coupling Reactions

The boron-doped polycyclic aromatic hydrocarbons (PAHs) have attracted ongoing attention in the field of optoelectronic materials due to their unique optical and redox properties. To investigate the effect of tetracoordinate boron in PAHs bearing N-heterocycles (indole and carbazole), a facile approach to four-coordinate boron-doped PAHs was developed, which does not require elevated temperature and pre-synthesized functionalized boron reactants. Five tetracoordinate boron-doped PAHs (NBNN-1 – NBNN-5) were synthesized with different functional groups. Two of them (NBNN-1 and NBNN-2) could further undergo oxidative coupling reactions to form fused off-plane tetracoordinate boron-doped PAHs NBNN-1f and NBNN-2f. Compared to the three-coordinate boron-doped counterparts, the UV/Vis absorption and fluorescent emission are significantly red-shift. Unlike the distinct impact of coordination number of boron on optoelectronic properties, the difference of functional groups on the boron atom has negligible impact on their optical and electrochemical properties. The compounds NBNN-1f and NBNN-2f show aggregation-induced emission.

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