Progress in the P(III)→P(V) Rearrangement Reaction of Phosphine Chlorides and Hydroxyl Containing Compounds

doi:10.6023/cjoc202406052

Abstract

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.

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

Cite this article

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.

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Fig. & Tab. 18

Scheme 1. Several synthetic strategies for pentavalent organophosphorus compounds

Scheme 2. [2,3] rearrangement of unsaturated alcohols with phosphine chlorides

Scheme 3. [2,3] rearrangement of propargyl/allenic alcohols with Ph2PCl

Scheme 4. [2,3] rearrangement tandem reaction of propargyl alcohols 1-5 with phosphine chlorides

Scheme 5. [2,3] rearrangement of cyclohexenol 1-7 with Ph2PCl

Scheme 6. [2,3] rearrangement of acyclic chiral allylic alcohols with Ph2PCl

Scheme 7. [2,3] rearrangement of cycloprpenyl alcohols with Ph2PCl

Scheme 8. [2,3] rearrangement of electron-poor allylic alcohols with phosphine chlorides

Scheme 9. Deoxygenative rearrangement of benzyl alcohols with Ph2PCl and its mechanism

Scheme 10. Cascade radical reaction of homoallylic alcohols, phosphine chlorides and fluoroalkyl iodide and its mechanism

Scheme 11. Reaction of aliphatic carboxylic acids with Ph2PCl and its mechanism

Scheme 12. Deoxygenative phosphorylation of aromatic carboxylic acids with Ph2PCl

Scheme 13. Synthesis of phosphinic amides from oximes and phosphine chlorides

Scheme 14. Ring-opening rearrangement of cyclobutanone oximes wth phosphine chlorides

Scheme 15. Proposed mechanism of reaction between cyclobutanone oximes and phosphine chlorides

Scheme 16. Reaction of hydroxylamine with phosphine chlorides

Scheme 17. (a) Computed energy profiles and the relative energies (kJ/mol); (b) Contours (isovalue=0.007) of the spin density of phosphoryl and amino radicals

Scheme 18. Rearrangement of electron-poor phenylhydroxylamine with phosphine chlorides

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