Netherton M R, Fu G C
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA.
Org Lett. 2001 Dec 27;3(26):4295-8. doi: 10.1021/ol016971g.
Trialkylphosphines furnish unusual, sometimes unique, reactivity in a range of transformations. Unfortunately, their utility is compromised by their sensitivity to oxidation. We have examined a simple but powerful strategy for addressing this problem: convert air-sensitive trialkylphosphines into air-stable phosphonium salts via protonation on phosphorus. These robust salts serve as direct replacements for the corresponding phosphines (simple deprotonation under the reaction conditions by a Brønsted base liberates the trialkylphosphine) in a diverse set of applications. [reaction: see text]
三烷基膦在一系列转化反应中展现出不同寻常、有时甚至是独特的反应活性。不幸的是，它们对氧化的敏感性限制了其用途。我们研究了一种简单而有效的解决该问题的策略：通过磷原子上的质子化将对空气敏感的三烷基膦转化为空气稳定的鏻盐。在各种应用中，这些稳定的盐可直接替代相应的膦（在反应条件下通过布朗斯特碱进行简单的去质子化即可释放出三烷基膦）。[反应：见正文]
