A Superior Non-Symmetrical NCP Pincer Type Palladacycle Catalyst Precursor for the Coupling of Aryl Boronic Acids with Aryl Chlorides

Gilber R. Rosa; Gunter Ebeling; Jairton Dupont; Adriano L. Monteiro

doi:10.1055/s-2003-44352

SPECIALTOPIC

A Superior Non-Symmetrical NCP Pincer Type Palladacycle Catalyst Precursor for the Coupling of Aryl Boronic Acids with Aryl Chlorides

Gilber R. Rosa, Gunter Ebeling, Jairton Dupont*, Adriano L. Monteiro*
Laboratory of Molecular Catalysis, Institute of Chemistry, UFRGS, Av. Bento Gonçalves, 9500 Porto Alegre, RS Brazil
Fax: +55(51)33167304; e-Mail: almonte@iq.ufrgs.br;

Abstract

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Abstract

The air and water stable non-symmetrical pincer palladacycle [Me₂NCH₂(Cl)C=C(CH₂)₂OP(i-Pr)₂-kNkCkP]PdCl 5, easily prepared from the chloropalladation of the hetero-substituted alkyne Me₂NCH₂C≡C(CH₂)₂OP(i-Pr)₂, is a highly efficient catalyst precursor for the coupling of aryl boronic acids and aryl chlorides. Both electron-rich and electron-poor aryl chlorides are efficiently coupled in the presence of 5 to furnish the corresponding cross-coupled products in excellent yields, and a wide variety of functional groups are tolerated in both aryl chloride and aryl boronic acid.

Key words

palladacycles - cross-coupling - boronic acids - aryl chlorides - Suzuki coupling

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