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Synthesis 2010(18): 3037-3062  
DOI: 10.1055/s-0030-1257960
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

Transition-Metal-Catalyzed C-P Cross-Coupling Reactions

Florian M. J. Tappea,b, Verena T. Trepohla, Martin Oestreich*a
a Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstraße 40, 48149 Münster, Germany
Fax: +49(251)8336501; e-Mail: martin.oestreich@uni-muenster.de;
b NRW Graduate School of Chemistry, Westfälische Wilhelms-Universität, Corrensstraße 40, 48149 Münster, Germany
Further Information

Publication History

Received 23 April 2010
Publication Date:
04 August 2010 (online)

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Abstract

This review is a comprehensive account of transition-metal-catalyzed cross-coupling reactions to form C-P bonds. Organized according to the hybridization of the carbon coupling partner, the numerous phosphorus coupling partners are discussed individually. The several putative mechanisms of these transition-metal catalyses are also included, thereby providing insights into both the synthetic and the mechanistic aspects of this chemistry. A separate section is devoted to asymmetric C-P cross-couplings.

1 Introduction

1.1 Carbon Coupling Partners

1.2 Phosphorus Coupling Partners

2 C(sp²)-P Cross-Coupling

2.1 Elemental Phosphorus as Coupling Partner

2.2 Quaternization and Aryl Exchange at P(III): R3P as Coupling Partners

2.2.1 Quaternization

2.2.2 Aryl Exchange

2.3 Silyl- and Stannylphosphines as Coupling Partners

2.4 Secondary and Primary Phosphines and Derivatives Thereof as Coupling Partners

2.5 Phosphine Chlorides as Coupling Partners

2.6 Phosphites, Phosphonites, Phosphinites and Derivatives Thereof as Coupling Partners

2.7 Hypophosphorous Acid and Derivatives Thereof as Coupling Partners

2.7.1 Hypophosphorous Acid as Coupling Partner

2.7.2 Hypophosphorous Acid Esters (Alkyl Phosphinates) as Coupling Partners

2.8 Secondary Phosphine Oxides as Coupling Partners

2.9 Alkyl Alkylphosphinates and Derivatives Thereof as Coupling Partners

2.10 Dialkyl Phosphites and Derivatives Thereof as Coupling Partners

3 C(sp)-P Cross-Coupling

4 C(sp³)-P Cross-Coupling

5 Asymmetric Cross-Coupling Reactions

Key words

copper - cross-coupling - nickel - phosphines - palladium

79

See ref. 20 in ref. 80.