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

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• 作者：Rachel M. Lanigan ; Pavel Starkov ; Tom D. Sheppard
• 刊名：The Journal of Organic Chemistry
• 出版年：2013
• 出版时间：May 3, 2013
• 年：2013
• 卷：78
• 期：9
• 页码：4512-4523
• 全文大小：522K
• 年卷期：v.78,no.9(May 3, 2013)
• ISSN：1520-6904

文摘

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.