General Synthesis and Catalytic Applications of Di(1-adamantyl)alkylphosphines and their Phosphonium Salts

Amit Tewari; Martin Hein; Alexander Zapf; Matthias Beller

doi:10.1055/s-2004-822313

PAPER

General Synthesis and Catalytic Applications of Di(1-adamantyl)alkylphosphines and their Phosphonium Salts

Amit Tewari^a, Martin Hein*^a, Alexander Zapf^b, Matthias Beller*^b
^a Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany
Fax: +49(381)4986412; e-Mail: martin.hein@chemie.uni-rostock.de;
^b Leibniz-Institut für Organische Katalyse an der Universität Rostock e.V, Buchbinderstr. 5-6, 18055 Rostock, Germany
Fax: +49(381)4669324; e-Mail: matthias.beller@ifok.uni-rostock.de;

Abstract

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Abstract

An improved synthesis of di(1-adamantyl)alkylphosphines by alkylation of di(1-adamantyl)phosphine followed by deprotonation of the resulting phosphonium halide is described. Compared to previous protocols for the synthesis of this class of compounds, the procedure does not require chlorination of the secondary phosphine by phosgene, or formation of sensitive lithium di(1-adamantyl)phosphide. Selected examples of the prepared phosphonium salts and phosphines are shown to be excellent ligands for the palladium-catalyzed cross-coupling reaction of chloroarenes with arylboronic acids.

Key words

adamantylphosphines - aryl chlorides - palladium - phosphine ligands - Suzuki reaction

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References

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