Synthesis 2003(3): 0455-0467
DOI: 10.1055/s-2003-37355
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Cross-Coupling Reaction of a Chiral Ferrocenyl Zinc Reagent with Aromatic Bromides: Application to the Design of Chiral Octupoles­ for Second Harmonic Generation

Victor Mamanea, Isabelle Ledoux-Rakc, Sandrine Deveaub, Joseph Zyssb, Olivier Riant*a,
a Laboratoire de Catalyse Moléculaire, ICMO, Université Paris-Sud, 91405 Orsay Cedex, France
e-Mail: riant@chim.ucl.ac.be;
b Laboratoire de Photonique Quantique et Moléculaire , Ecole Normale Supérieure de Cachan (UMR CNRS 8537) Institut d’Alember, (IFR 121) - 61 avenue du Président Wilson 94235 Cachan Cedex, France
Further Information

Publication History

Received 7 November 2002
Publication Date:
19 February 2003 (online)

Abstract

Palladium catalyzed cross coupling reaction of a chiral ferrocenylzinc reagent with aryl bromides allowed the introduction of a planary chiral ferrocenyl subunit on an aryl fragment. Using this method, new C3 symmetric chiral architecture bearing organometallic donor-acceptor fragments were assembled starting from a common tris aldehyde precursor. The non- linear optical properties were measured using the Harmonic Light Scattering method and the potentiality for the new chromophores to behave as octupoles is also discussed.

1

New address : Laboratoire de Chimie Organique et Médicinale, Département de Chimie, Place Louis Pasteur 1, Université catholique de Louvain, 1348 Louvain la neuve, Belgium. Fax : +32(10)474168.

2

Chem. Phys. 1999, 245; special issue devoted to molecular nonlinear optics.