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Synlett 2012(8): 1132-1153  
DOI: 10.1055/s-0031-1290672
ACCOUNT
© Georg Thieme Verlag Stuttgart ˙ New York

The Recent Development of Phosphine Ligands Derived from 2-Phosphino-Substituted Heterocycles and Their Applications in Palladium-Catalyzed Cross-Coupling Reactions

Shun Man Wong, Chau Ming So, Fuk Yee Kwong*
State Key Laboratory of Chirosciences and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong
e-Mail: bcfyk@inet.polyu.edu.hk;
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Publication History

Received 3 September 2011
Publication Date:
26 April 2012 (online)

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Abstract

Heterocyclic phosphines have long been used as unique and efficient ligands for palladium-catalyzed cross-coupling reactions. The simplest ligand, trifurylphosphine, has become one of the most classical heterocyclic phosphines for coupling reactions since its first application in the Stille coupling reaction in 1988. In recent decades, palladium catalyst systems derived from highly diverse and innovative heterocyclic phosphines have shown excellent catalytic activities in cross-coupling reactions. In this account, we discuss the recent development and applications of heterocyclic phosphine ligands, highlighting the synthetic pathways used to prepare the ligands. The sections are categorized by the different palladium-catalyzed cross-coupling methodologies.

1 Introduction

2 Carbon-Carbon Bond-Forming Reactions

2.1 Suzuki-Miyaura Coupling Reaction

2.2 Heck Reaction

2.3 Sonogashira Reaction

2.4 Cyanation

3 Carbon-Nitrogen Bond-Forming Reactions

4 Carbon-Oxygen Bond-Forming Reactions

4.1 Carbon-Oxygen Coupling Reaction

4.2 Hydroxylation

5 Carbon-Boron Bond-Forming Reactions

6 Conclusion

Key words

ligands - cross-coupling - catalysis - phosphines - palladium

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53

Wong, S. M.; So, C. M.; Yeung, C. C.; Kwong, F. Y. unpublished results.