Synthesis 2005(14): 2287-2292  
DOI: 10.1055/s-2005-870013
PAPER
© Georg Thieme Verlag Stuttgart · New York

Palladium-Phosphinous Acid Catalyzed Cross-Coupling of Aryl Halides Using a Hypervalent Phenylsilane in Water

Rachel Lerebours, Christian Wolf*
Department of Chemistry, Georgetown University, Washington, DC 20057, USA
Fax: +1(202)6876209; e-Mail: cw27@georgetown.edu;
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Publikationsverlauf

Received 28 February 2005
Publikationsdatum:
13. Juli 2005 (online)

Abstract

A palladium-phosphinous acid catalyzed NaOH-promoted cross-coupling methodology that affords biaryls from tetrabutylammonium triphenyldifluorosilicate and aryl halides in good to high yields has been developed. The coupling proceeds in aqueous 0.5 M NaOH solution in the absence of organic co-solvents and does not require inert atmosphere, which greatly facilitates operation and catalyst handling.

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Bond dissociation energies for PhX; X = Cl: 96 kcal/mol, X = Br: 81 kcal/mol, X = I: 65 kcal/mol.