氯化膦与羟基化合物参与的P(III)→P(V)重排反应研究进展

doi:10.6023/cjoc202406052

摘要/Abstract

五价磷P(V)有机物广泛应用于合成、材料、生物、医药和农业等领域,其合成方法研究一直吸引着有机化学家的兴趣。从三价磷P(III)到五价磷P(V)的重排反应(P(III)→P(V))是合成五价磷有机物的重要策略。经典的Michaelis-Arbuzov反应通过亲核性亚磷酸酯(P(OR)₃)与卤代烃发生P(III)→P(V)重排反应,为膦酸酯的合成提供了重要方法。与此相反,亲电性氯化膦(ClPR¹R²)与羟基化合物(RA-OH)作用可原位生成RA-O-PR¹R²中间体,继而发生A-O键断裂和A-P键形成从而实现P(III)→P(V)重排,也为五价磷有机物的合成提供了有效方法。这两类P(III)→P(V)重排反应都是在磷的强亲氧性驱动下实现的,具有原子经济性高、底物简单易得等优点。本文主要综述了氯化膦与不同类型羟基化合物(如：醇、羧酸、肟和羟胺等)的P(III)→P(V)重排反应,分别用于氧膦、膦酸酯、磷酰胺等五价磷化合物的合成。

关键词: 氯化膦, 羟基化合物, 有机磷化合物, 重排反应

Pentavalent organophosphorus compounds are widely used in synthesis, materials, biology, medicine, agriculture, etc, and their synthetic methods have attracted a long-term interest from organic chemists. The P(III)→P(V) rearrangement from trivalent organophosphorus compounds is an important strategy for the synthesis of pentavalent organophosphorus compounds. The classical Michaelis-Arbuzov reaction, which involves a P(III)→P(V) rearrangement reaction between a nucleophilic phosphite (P(OR)₃) and alkyl halides, provides an important method for the synthesis of phosphonates. In contrast, the reaction between electrophilic phosphine chlorides (ClPR¹R²) and hydroxyl containing compounds (RA-OH), by generating a RA-O-PR¹R² intermediate in situ followed by A-O bond cleavage and A-P bond formation thus to realize P(III)→P(V) rearrangement, also provides an effective synthetic method for pentavalent organophosphorus compounds. The two types of P(III)→P(V) rearrangement reactions are both driven by the oxophilicity of phosphorus, bearing the advantages of high atom economy and readily available substrates. This article mainly reviews the P(III)→P(V) rearrangement reactions of phosphine chlorides with different types of hydroxyl containing compounds, such as alcohols, carboxylic acids, oximes, hydroxylamines, etc, for the synthesis of phosphine oxides, phosphonates, and phosphoric amides, respectively.

Key words: phosphine chlorides, hydroxyl containing compounds, organophosphorus compounds, rearrangement

引用此文

杨露露, 易翠, 吴佳乐, 张宇轩, 白美琪, 李洋, 徐四龙. 氯化膦与羟基化合物参与的P(III)→P(V)重排反应研究进展[J]. 有机化学, doi: 10.6023/cjoc202406052.

Yang LuLu, Yi Cui, Wu Jiale, Zhang Yuxuan, Bai Meiqi, Li Yang, Xu Silong. Progress in the P (III)→P (V) Rearrangement Reaction of Phosphine Chlorides and Hydroxyl Containing Compounds[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202406052.

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