Towards the preparation of modified chiral electrodes for heterogeneous asymmetric catalysis: synthesis and electrochemical properties of (S,S)-5,5′-bis-[3-(3-methyl-pentyl)-thiophen-2-yl]-[2,2′]-bipyridine

The aim of this work is the electrochemical synthesis of a new type of material possessing the properties of organic conductive polymers along with those of organometallic complexes, for their use in asymmetric heterogeneous catalysis. The synthesis of (S,S)-5,5′-bis-[3-(3-methyl-pentyl)-thiophen-2-yl]-[2,2′]-bipyridine is described in nine steps with good yields. This chiral synthon has been successfully used as ligand in the homogeneous asymmetric catalytic reduction of acetophenone by hydride transfer with various transition metals. Its electro(homo- or co-)polymerization failed until now, probably due to the electron deficiency of this monomer.