Arbuzov Reaction
Michaelis-Arbuzov Reaction

The reaction of a trialkyl phosphite with an alkyl halide to produce an alkyl phosphonate. The first step involves nucleophilic attack by the phosphorus on the alkyl halide, followed by the halide ion dealkylation of the resulting trialkoxyphosphonium salt.

This reaction sees extensive application in the preparation of phosphonate esters for use in the Horner-Emmons Reaction.

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Mechanism of the Arbuzov Reaction

Recent Literature

Lewis Acid-Mediated Michaelis-Arbuzov Reaction at Room Temperature: A Facile Preparation of Arylmethyl/Heteroarylmethyl Phosphonates
G. G. Rajeshwaran, M. Nandakumar, R. Sureshbabu, A. K. Mohanakrishnan, Org. Lett., 2011, 13, 1270-1273.

Generation of Phosphoranes Derived from Phosphites. A New Class of Phosphorus Ylides Leading to High E Selectivity with Semi-stabilizing Groups in Wittig Olefinations
V. K. Aggarwal, J. R. Fulton, C. G. Sheldon, J. de Vicente, J. Am. Chem. Soc., 2003, 125, 6034-6035.

Reliable and Versatile Synthesis of 2-Aryl-Substituted Cinnamic Acid Esters
A. Ianni, S. R. Waldvogel, Synthesis, 2006, 2103-2112.

Copper-Catalyzed Aerobic Oxidative/Decarboxylative Phosphorylation of Aryl Acrylic Acids with P(III)-Nucleophiles
B. Xiong, L. Si, L. Zhu, Y. Liu, W. Xu, K.-W. Tang, S.-F. Yin, P.-C. Qian, W.-Y. Wong, J. Org. Chem., 2023, 88, 12502-12518.