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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|
|Electronic Publication Date:||10-Jan-2017|
|Citation:||Carrow, Bradley P., Chen, Liye. (2017). Tri(1-adamantyl)phosphine: Exceptional Catalytic Effects Enabled by the Synergy of Chemical Stability, Donicity, and Polarizability. Synlett, 28 (03), 280 - 288. doi:10.1055/s-0036-1588128|
|Pages:||28, 280 - 288|
|Type of Material:||Journal Article|
|Version:||Final published version. Article is made available in OAR by the publisher's permission or policy.|
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