Issue 2, 2010
From the journal:

Chemical Society Reviews

Sterically demanding trialkylphosphines for palladium-catalyzed cross coupling reactions—alternatives to PtBu3

Christoph A. Fleckensteinab  and  Herbert Plenio*a  

* Corresponding authors

a Anorganische Chemie im Zintl-Institut, TU Darmstadt, Petersenstr. 18, 64287 Darmstadt, Germany
E-mail: plenio@tu-darmstadt.de

b BASF-The Chemical Company, BASF SE, GCI/P-M311, 67056 Ludwigshafen, Germany
E-mail: christoph.a.fleckenstein@basf.com

Abstract

The strong electron-donation and the steric bulk of trialkylphosphines renders them as very useful ligands for palladium-catalyzed cross coupling reactions. This critical review reports on the synthesis of two families of trialkylphosphines (diadamantylalkylphosphines, fluorenyldialkylphosphines) and the properties of the respective palladium complexes in various cross coupling reactions, which evolved as alternatives to the classical Pd/PtBu3 system. In contrast to the latter phosphine the new classes of ligands are characterized by a highly flexible ligand design, which allows the fine tuning of catalytic properties to the specific needs of certain substrates and also enables the attachment of additional tags to impart certain useful properties onto the respective phosphines (179 references).

Graphical abstract: Sterically demanding trialkylphosphines for palladium-catalyzed cross coupling reactions—alternatives to PtBu3

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Article information

DOI
https://doi.org/10.1039/B903646F
Article type
Critical Review
Submitted
15 Jul 2009
First published
16 Oct 2009

Chem. Soc. Rev., 2010,39, 694-711

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Sterically demanding trialkylphosphines for palladium-catalyzed cross coupling reactions—alternatives to PtBu3

C. A. Fleckenstein and H. Plenio, Chem. Soc. Rev., 2010, 39, 694 DOI: 10.1039/B903646F

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