Chemistry Reference
In-Depth Information
Strategies in Organic Synthesis for
Condensed Arenes, Coronene, and Graphene
Anne-Florence Tran-Van and Hermann A. Wegner
Abstract Graphene-type structures are without doubt one of the most exciting
carbon-based materials known. Although graphene is mostly prepared by physical
methods (CVD, exfoliation), organic synthesis represents a powerful alternative to
access graphene-type structures in a selective and reproducible manner. Although
graphene has been hyped as a “new” material, the resemblence to polycyclic
aromatic hydrocarbons (PAHs) offers a long history in organic chemistry on
which all new endeavors are built. In this review we demonstrate the state-of-the-
art of organic synthetic strategies for the preparation of graphene-type structures on
selected examples.
Keywords Catalysis
Coupling reactions
Graphene
Organic synthesis
Polycyclic aromatic hydrocarbons
Contents
1 Introduction .................................................................................. 122
2 Synthetic Methods to Assemble Graphene-Type Structures ............................... 122
2.1 Pioneering Synthesis of PAHs . ....................................................... 124
2.2 Syntheses via the Diels-Alder Reaction . . ........................................... 126
2.3 Cyclotrimerization . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 132
2.4 Aryl-Aryl-Coupling Reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 137
2.5 Annulation Reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 142
2.6 Ring Closing Metathesis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................ 146
