Phosphorus-based fatty acid methyl esters

•Various strategies to introduce phosphorus arms to the fatty acid renewable resources are examined.•Eleven novel phosphorus-based fatty acid methyl esters are isolated.•Bulky lithiated phosphines react classically to brominated fatty esters to afford the mono-addition product.•Symmetrically stable diesters are successfully prepared by reacting ArP(O)Cl2 with two hydroxyl fatty esters.

With the aim of designing novel transformable fatty acid diesters, various strategies for introducing phosphorus arms to the fatty backbone have been examined. While lithiated phosphine reacts classically to brominated fatty esters to afford the mono-addition product, the synthesis of phosphorylated diesters was found to be difficult, a fact related to the bulkiness of fatty acids and phosphine reagents. A base-induced dehydrochlorination reaction using ArPCl2 and hydroxy-terminated fatty esters resulted in metastable diester for which hydrolytic cleavage undergo phosphine oxidation and expulsion of one fatty chain. Alternatively, ArPOCl2 alleviates this drawback and provides stable, phosphorylated fatty acid diesters.

Graphical abstractVarious strategies for introducing phosphorus arms to the fatty backbone have been examined enabling the design of novel phosphorus-based building blocks.Figure optionsDownload full-size imageDownload as PowerPoint slide