Tris(2,2,2-trifluoroethyl) borate

Tris(2,2,2-trifluoroethyl) borate, also commonly referred to as the Sheppard amidation reagent,[2] is a chemical compound with the formula B(OCH2CF3)3.

The latter is more convenient for larger scale preparations due to its low cost and ease of handling.

It has been shown to promote the direct formation of amides[4][5][6][7] from carboxylic acids and amines as well as the formation of imines[8] from amines or amides with carbonyl compounds.

[clarification needed][6][9] It has also been shown to mediate formylation of amines, via transamidation of dimethylformamide.

It is a strong Lewis acid (acceptor number = 66, Gutmann-Beckett method).

Tris(2,2,2-trifluoroethyl) borate molecule