Chinese Journal of Organic Chemistry >
Progress in the P(III)→P(V) Rearrangement Reaction of Phosphine Chlorides and Hydroxyl Containing Compounds
Received date: 2024-06-30
Revised date: 2024-08-27
Online published: 2024-09-10
Supported by
National Natural Science Foundation of China(22471208); National Natural Science Foundation of China(22471218)
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 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) generaes 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. Two types of the 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. 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 are mainly reviewed, respectively.
Lulu Yang , Cui Yi , Jiale Wu , Yuxuan Zhang , Meiqi Bai , Yang Li , Silong Xu . Progress in the P(III)→P(V) Rearrangement Reaction of Phosphine Chlorides and Hydroxyl Containing Compounds[J]. Chinese Journal of Organic Chemistry, 2024 , 44(12) : 3639 -3646 . DOI: 10.6023/cjoc202406052
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