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Tri(1-adamantyl)phosphine: Exceptional Catalytic Effects Enabled by the Synergy of Chemical Stability, Donicity, and Polarizability
Synlett ( IF 1.7 ) Pub Date : 2017-01-10 , DOI: 10.1055/s-0036-1588128 Brad Carrow , Liye Chen
Synlett ( IF 1.7 ) Pub Date : 2017-01-10 , DOI: 10.1055/s-0036-1588128 Brad Carrow , Liye Chen
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
中文翻译:
三(1-金刚烷基)膦:通过化学稳定性、Donicity 和极化性的协同作用实现卓越的催化效果
三(1-金刚烷基)膦,一种简单但长期缺席的均质膦,终于被制备出来。这种化合物的简单性吸引了其卓越的性能。电子释放特性使所有其他烷基膦黯然失色。膦的几何形状和整体尺寸也比预期的更紧凑,这可能是分散力的结果。我们认为,在 Suzuki-Miyaura 偶联反应过程中,Pd-PAd3 催化剂的显着性能是由于三类金刚石碎片产生的选择性、对环金属化或 P-C 键断裂的显着抵抗以及显着的极化性。还描述了相关分析,该分析支持极化率作为对叔膦性质的潜在普遍影响。
更新日期:2017-01-10
中文翻译:
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三(1-金刚烷基)膦:通过化学稳定性、Donicity 和极化性的协同作用实现卓越的催化效果
三(1-金刚烷基)膦,一种简单但长期缺席的均质膦,终于被制备出来。这种化合物的简单性吸引了其卓越的性能。电子释放特性使所有其他烷基膦黯然失色。膦的几何形状和整体尺寸也比预期的更紧凑,这可能是分散力的结果。我们认为,在 Suzuki-Miyaura 偶联反应过程中,Pd-PAd3 催化剂的显着性能是由于三类金刚石碎片产生的选择性、对环金属化或 P-C 键断裂的显着抵抗以及显着的极化性。还描述了相关分析,该分析支持极化率作为对叔膦性质的潜在普遍影响。