C3-Symmetric Pyridine and Bipyridine Derivatives: Simple Preparation by Cyclocondensation and 2D Self-Assembly at a Solution-Graphite Interface
J. Dash, D. Trawny, J. P. Rabe, H.-U. Reissig – 2015
The efficient preparation of four C3-symmetric (star-shaped) pyridine and bipyridine derivatives is reported. The key steps are Suzuki couplings of 4-pyridyl nonaflates with 4-acetyl-phenylboronic acid followed by an acid-promoted cyclocondensation reaction converting the methyl ketone moiety into the central benzene ring of the target compounds. Based on STM studies at a graphite–solution interface the two-dimensional arrangements of the compounds are discussed, showing the influence of the pyridine substitution pattern.