Synthesis 2003(2): 0302-0306
DOI: 10.1055/s-2003-36833
PAPER
© Georg Thieme Verlag Stuttgart · New York

Cross-Coupling of Aryl Halides and Triflates with Intramolecularly Stabilized Group 13-Metal Alkylating Reagents in the Presence of Mixed-Metal Catalysts

Margarita Shenglofa, Dmitri Gelmana, Bernd Heymerb, Herbert Schumannb, Gary A. Molanderc, Jochanan Blum*a
a Department of Organic Chemistry, Hebrew University, Jerusalem 91904, Israel
Fax: +972(2)6513832; e-Mail: jblum@chem.ch.huji.ac.il;
b Institut für Chemie, Technische Universität, 10623 Berlin, Germany
Fax: +49(30)31422168; e-Mail: schumann@chem.tu-berlin.de;
c Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6323 USA
Fax: +1(215)5737165; e-Mail: gmolandr@sas.upenn.edu;
Further Information

Publication History

Received 7 November 2002
Publication Date:
22 January 2003 (online)

Abstract

In the presence of tertiary phosphines, the palladium-containing mixed-metal complexes [(CO)4Fe(µ-PPh2)Pd(µ-Cl)]2 (1) and [(CO)3Co]2(µ-CO)Pd[µ-(Ph2PCH2)2] (2) catalyze the cross-coupling of aryl triflates and halides (including chlorides) with intramolecularly stabilized dialkylaluminum, -gallium and -indium reagents 3-8. The reactions are high yielding, and homocoupling and hydrodehalogenation processes are minimal even when the alkyl moieties of the alkylating reagents contain β-hydrogen atoms. As the components of the mixed-metal complexes are either poor catalysts, or completely inactive, the high catalytic activity of 1 and 2 is attributed to synergism between the different metal nuclei of the catalysts.

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