Synthesis of Phosphonates via Michaelis-Arbuzov Reaction

化学 磷化氢 产量(工程) 烷基 卤化物 反应条件 溶剂 有机化学 组合化学 催化作用 冶金 材料科学
作者
B. Hari Babu,Gandavaram Syam Prasad,C. Naga Raju,Mandava Venkata Basaveswara Rao
出处
期刊:Current Organic Synthesis [Bentham Science Publishers]
卷期号:14 (6): 883-903 被引量:39
标识
DOI:10.2174/1570179414666161230144455
摘要

Background: Michaelis–Arbuzov reaction has played a key role for the synthesis of dialkyl or diaryl phosphonates by reacting various alkyl or aryl halides with trialkyl or triaryl phosphite. This reaction is very versatile in the formation of P-C bond from the reaction of aliphatic halides with phosphinites or phosphites to yield phosphonates, phosphinates, phosphine oxides. The Arbuzov reaction developed some methodologies, possible mechanistic pathways, selectivity, potential applications and biologically active various phosphonates. Objective: The synthesis of phosphonates via Michaelis–Arbuzov reaction with many new and fascinating methodologies were developed and disclosed in the literature, and these are explored in this review. Conclusion: This review has discussed past developments and vast potential applications of Arbuzov reaction in the synthesis of organophosphonates. As presented in this review, various synthetic methodologies were developed to prepare a large variety of phosphonates. Improvements in the reaction conditions of Lewis-acid mediated Arbuzov rearrangement as well as the development of MW-assisted Arbuzov rearrangement were discussed. Finally, to achieve high selectivities and yields, fine-tuning of reaction conditions including solvent type, temperature, and optimal reaction times to be considered.
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