Reactivity of Alkynyl Phosphines with Lewis Acids for the Synthesis of Allenic Phosphonium Borate Zwitterions,Zeitschrift für anorganische und allgemeine Chemie

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Reactivity of Alkynyl Phosphines with Lewis Acids for the Synthesis of Allenic Phosphonium Borate Zwitterions
Zeitschrift für anorganische und allgemeine Chemie ( IF 1.1 ) Pub Date : 2023-01-13 , DOI: 10.1002/zaac.202200383
Lucas Christian Torres ₁ , Amandeep Brar ₂ , Jesse LeBlanc ₂ , Clive Boateng Ameyaw ₂ , Christopher Blain Caputo ₁

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The reactivity of alkynylphosphines with Lewis acidic boranes has been well established in recent years thanks to the advent of frustrated Lewis pairs (FLPs), often leading to a 1,1-carboboration reaction and the formation of an intramolecular phosphinoborane FLP. Our group recently discovered that introduction of an ionizable group in the γ-position of an alkynylphosphine result in an unexpected rearrangement reaction to yield zwitterionic allenic-phosphonium borate products which are produced via a transient 3-coordinate phosphonium allenylidene. Herein, we describe how substituent effects on the γ-carbon impact this reactivity and explore how bis(alkynyl)phosphines behave under similar reaction conditions.

中文翻译：

炔基膦与路易斯酸的反应性用于合成丙二烯硼酸盐两性离子

近年来，由于受挫路易斯对 (FLP) 的出现，炔基膦与路易斯酸性硼烷的反应性得到了很好的证实，通常会导致 1,1-碳硼化反应和分子内膦基硼烷 FLP 的形成。我们小组最近发现，在炔基膦的 γ 位引入可电离基团会导致意想不到的重排反应，从而产生两性离子丙二烯-硼酸盐产物，这些产物是通过瞬时 3 配位亚丙基膦产生的。在此，我们描述了 γ- 碳的取代基效应如何影响这种反应性，并探讨了双（炔基）膦在类似反应条件下的行为方式。

更新日期：2023-01-13

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