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Direct Synthesis of Amides from Carboxylic Acids and Amines Using B(OCH2CF3)3

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journal contribution
posted on 16.12.2015, 22:45 by Rachel M. Lanigan, Pavel Starkov, Tom D. Sheppard
B­(OCH2CF3)3, prepared from readily available B2O3 and 2,2,2-trifluoroethanol, is as an effective reagent for the direct amidation of a variety of carboxylic acids with a broad range of amines. In most cases, the amide products can be purified by a simple filtration procedure using commercially available resins, with no need for aqueous workup or chromatography. The amidation of N-protected amino acids with both primary and secondary amines proceeds effectively, with very low levels of racemization. B­(OCH2CF3)3 can also be used for the formylation of a range of amines in good to excellent yield, via transamidation of dimethylformamide.