期刊
SYNLETT
卷 28, 期 3, 页码 280-288出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0036-1588128
关键词
phosphine; ligand; catalysis; cross-coupling; palladium; diamondoid
资金
- Princeton University
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-PAd(3) 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
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