Palladium-Catalyzed Double Cross-Coupling Reactions of Organodimetallic Reagents Leading to Polycyclic Aromatic Hydrocarbons

2013 ◽  
Vol 2013 (36) ◽  
pp. 8069-8081 ◽  
Author(s):  
Masaki Shimizu ◽  
Tamejiro Hiyama
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Aromatic Hydrocarbons ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Polycyclic Aromatic ◽  
Palladium Catalyzed ◽  
Double Cross

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.

New Synthesis of Dibenzofulvenes by Palladium-Catalyzed Double Cross-Coupling Reactions

2012 ◽  
Vol 65 (9) ◽  
pp. 1277 ◽  
Author(s):  
Masaki Shimizu ◽  
Ikuhiro Nagao ◽  
Shin-ichi Kiyomoto ◽  
Tamejiro Hiyama
Keyword(s):  
Cross Coupling ◽  
Synthetic Methods ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
New Synthesis ◽  
Palladium Catalyzed ◽  
Double Cross

Palladium-catalyzed double cross-coupling reactions of 1,1-bis(pinacolato)borylalk-1-enes with 2,2′-dibromobiaryls and of 9-stannafluorenes with 1,1-dibromoalk-1-enes have been demonstrated to serve as new synthetic methods for dibenzofulvenes.

ChemInform Abstract: New Synthesis of Dibenzofulvenes by Palladium-Catalyzed Double Cross-Coupling Reactions.

ChemInform ◽  
2013 ◽  
Vol 44 (11) ◽  
pp. no-no
Author(s):  
Masaki Shimizu ◽  
Ikuhiro Nagao ◽  
Shin-ichi Kiyomoto ◽  
Tamejiro Hiyama
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
New Synthesis ◽  
Palladium Catalyzed ◽  
Double Cross

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.

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