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21.14.1.1.1 Method 1: The Arbuzov Reaction: Acylation of Phosphorus(III) Compounds

DOI: 10.1055/sos-SD-021-00911

Whitehead, A.; Sieck, S. R.; Mukherjee, S.; Hanson, P. R.Science of Synthesis, (200521907.

The most general approach to this subclass of compounds is the MichaelisArbuzov reaction of trialkyl or triaryl phosphites with acyl chlorides; it remains the most widely employed route for the generation of acylphosphonates (see Sections 21.14.1.2.1.3, 21.14.1.2.2.3, 21.14.1.2.3.1, 21.14.1.2.7, and 21.14.1.2.7.2). While having been extensively studied, areas of interest remain. One area of continued investigation is the generation of nonsymmetrically substituted acylphosphonates from mixed phosphite precursors.[‌4‌] This method requires differentiated reactivity between the different phosphite substituents. For example, treatment of benzyl dimethyl phosphite (1) with an acid chloride gives a mixture of symmetric and nonsymmetric acylphosphonates, separable by distillation, resulting in the nonsymmetric acylphosphonate 2 in moderate yield (Scheme 1).[‌4‌]

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