Tri(1-adamantyl)phosphine: Exceptional Catalytic Effects Enabled by the Synergy of Chemical Stability, Donicity, and Polarizability

Brad P. Carrow; Liye Chen

doi:10.1055/s-0036-1588128

Synlett, Inhaltsverzeichnis

Synlett 2017; 28(03): 280-288
DOI: 10.1055/s-0036-1588128

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Tri(1-adamantyl)phosphine: Exceptional Catalytic Effects Enabled by the Synergy of Chemical Stability, Donicity, and Polarizability

Brad P. Carrow*

Department of Chemistry, Princeton University, Princeton, NJ 08544, USA eMail: bcarrow@princeton.edu

,

Liye Chen

Department of Chemistry, Princeton University, Princeton, NJ 08544, USA eMail: bcarrow@princeton.edu

› Institutsangaben

Abstract

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Abstract

Tri(1-adamantyl)phosphine, a simple yet long-absent homoleptic phosphine, has finally been prepared. The simplicity of this compound beguiles its exceptional properties. The electron-releasing character eclipses all other alkylphosphines. The phosphine geometry and overall size are also more compact than anticipated, which may occur as a result of dispersion forces. We believe the donicity, marked resistance towards cyclometallation or P−C bond scission, and also substantial polarizability engendered by the three diamondoid fragments together account for the phenomenal performance of Pd-PAd₃ catalysts during Suzuki–Miyaura coupling reactions. A correlation analysis is also described that provides support for polarizability as a potentially general influence on the properties of tertiary phosphines.

1 Introduction

2 Synthesis of Tri(1-adamantyl)phosphine

3 Reactions of Tri(1-adamantyl)phosphine Palladium Complexes

4 Electronic and Steric Properties of Tri(1-adamantyl)phosphine

5 Conclusion

Key words

phosphine - ligand - catalysis - cross-coupling - palladium - diamondoid

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Referenzen

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