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Chlorine-Free Synthesis of P-Esters: Microwave-Assisted Direct Esterification of Phosphinic, Phosphonic, as Well as Phosphoric Acid Derivatives
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DOI：10.1002/cmtd.70141.png)
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Abstract
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It is well-known that heteroatomic acids, such as P- and S-acids, do not undergo direct esterification with alcohols. For this, the different P- and S-esters are usually synthesized from the corresponding P- and S-chlorides. However, this approach is not “green” due to the formation of the hydrochloride by-product. In this article, we focus on the P-acid → P-ester transformations. It was a practical innovation to find that phosphinic and phosphonic acids, along with alkoxyphosphoric acids, took part under microwave irradiation in a solvolytic-type esterification with alcohols to afford the corresponding phosphinates, monoalkyl phosphonates, and dialkyl phosphates, respectively. All esterifications were promoted by a suitable ionic liquid catalyst. The scope, optimal conditions, energetics, and mechanistic insights are discussed in this minireview. The second and third alkyl group may be introduced by alkylating esterification to furnish dialkyl phosphonates and trialkyl phosphates, respectively.
Keywords:
direct esterification
microwave chemistry
P-acids
phosphorylation
theoretical calculations
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6.1
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