Stepwise Synthesis of Conjugatively Bridged Bipyridine Ligands from Thiophene and Alkyne Linkages

Sébastien Goeb; Antoinette De Nicola; Raymond Ziessel

doi:10.1055/s-2005-861847

PAPER

Stepwise Synthesis of Conjugatively Bridged Bipyridine Ligands from Thiophene and Alkyne Linkages

Sébastien Goeb, Antoinette De Nicola, Raymond Ziessel*
Laboratoire de Chimie Moléculaire, associé au CNRS, Université Louis Pasteur (ULP), Ecole de Chimie, Polymères, Matériaux de Strasbourg (ECPM), 25 rue Becquerel, 67087 Strasbourg, Cedex 02, France
Fax: +33(3)90242689; e-Mail: ziessel@chimie.u-strasbg.fr;

Abstract

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Abstract

The dual Sonogashira coupling reaction of 5,5′-dibromo-2,2′-bipyridine with TMS and CMe₂OH protected acetylene allows the synthesis of a disymmetrically functionalized building block which was selectively deprotected from the TMS or the 2-hydroxyprop-2-yl site. Various combinations allow the interconnection of the terminal alkyne to 3,4-dibutyl-2-iodothiophene or 3,4-dibutyl-2,5-diiodothiophene leading to bipyridine frameworks bearing two ethynylthiophene units or one thiophene/one acetylene function. It was possible to construct ditopic or tritopic bipyridine ligands where the chelating subunit is bridged by an 3,4-dibutyl-2,5-diethynylthiophene spacer and end-capped by a 3,4-dibutyl-2-ethynylthiophene stopper.

Keywords

multi-topic ligands - bipyridine - thiophene - alkyne spacer - palladium couplings

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Referenzen

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