Design and Development of Ligands for Palladium-Catalyzed Carbonylation Reactions

Dedicated to Professor Li-Xin Dai on the occasion of his 90^th birthday

Abstract

The palladium-catalyzed carbonylation reaction remains a challenging and significant research field in organic chemistry, and has emerged as a powerful and straightforward protocol for the preparation of various bioactive carbonyl compounds under quite mild reaction conditions. The achievements in this area are correlated to the design and development of versatile ligands that not only facilitate the catalytic transformation, but also provide additional control over the selectivity of the reactions. In this context, a variety of rationally designed ligands with different electronic and steric properties have been synthesized and applied in palladium-catalyzed carbonylation reactions in recent decades. This review focuses mainly on the strategy of ligand design and the results obtained with representative ligands that have different σ-donor properties in the intra- and intermolecular palladium-catalyzed carbonylation reactions of (pseudo)haloarenes with gaseous carbon monoxide and numerous types of nucleophiles. The current limitations and potential trends for further development of palladium-catalyzed carbonylation reactions are also highlighted.

1 Introduction

2 Phosphine Ligands

2.1 Monodentate Phosphines

2.1.1 Triphenylphosphine and Analogues

2.1.2 Di(1-adamantyl)-n-butylphosphine

2.1.3 Biaryl Monophosphines

2.2 Bidentate Phosphine Ligands

2.2.1 Alkyl-Bridged Diphosphines

2.2.2 Ferrocene-Based Bidentate Phosphines

2.2.3 Xantphos and Analogues

2.2.4 BINAP and Analogues

3 N-Heterocyclic Carbenes (NHCs)

4 Other Ligands

4.1 Nitrogen Ligands

4.2 Thiourea-Type Ligands

5 Summary and Outlook

Key words

carbonylation - carbon monoxide - catalysts - ligands - palladium

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