Thiophenes & thiazoles as advanced materials
Activation of the CH bond of heteroaromatic compounds with a transition metal catalyst is performed. Coupling reaction of thus formed metal species with various organic electrophiles to form carbon-carbon and carbon-heteroatom bonds is developed. Application of these reactions toward advanced organic materials and biologically active molecules is our major concern.
J. Am. Chem. Soc., 2003, 125, 1700
J. Am. Chem. Soc., 2004, 126 , 5074
J. Am. Chem. Soc. 2006, 128, 10930
J. Am. Chem. Soc. 2011, 133, 16734
New synthetic methodology of polythiophene synthesis with C-H coupling polymerization
Metalation at the 5-position of 2-chloro-3-hexylthiophene and 2-bromo-3-hexylthiophene with magnesium amide or the combination of catalytic secondary amine and Grignard reagent and following addition of a nickel catalyst induces polymerization affording highly regioregular head-to-tail-type poly(3-hexylthiophene).
Design and synthesis of regioregular head-to-tail-type linear and branched oligothiophens
Regioselective metalation of 3-hexylthiophene at the 5-position and following nickel-catalyzed coupling with halothiophene forms thiophene-thiophene bond. A variety of linear and branched oligothiophenes are synthesized highly efficiently.
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