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Direct Synthesis of Amides from Carboxylic Acids and Amines Using B(OCH(2)CF(3))(3)

[Image: see text] B(OCH(2)CF(3))(3), prepared from readily available B(2)O(3) 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 proced...

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Detalles Bibliográficos
Autores principales: Lanigan, Rachel M., Starkov, Pavel, Sheppard, Tom D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2013
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3671500/
https://www.ncbi.nlm.nih.gov/pubmed/23586467
http://dx.doi.org/10.1021/jo400509n
Descripción
Sumario:[Image: see text] B(OCH(2)CF(3))(3), prepared from readily available B(2)O(3) 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(OCH(2)CF(3))(3) can also be used for the formylation of a range of amines in good to excellent yield, via transamidation of dimethylformamide.