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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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
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author Lanigan, Rachel M.
Starkov, Pavel
Sheppard, Tom D.
author_facet Lanigan, Rachel M.
Starkov, Pavel
Sheppard, Tom D.
author_sort Lanigan, Rachel M.
collection PubMed
description [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.
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spelling pubmed-36715002013-06-05 Direct Synthesis of Amides from Carboxylic Acids and Amines Using B(OCH(2)CF(3))(3) Lanigan, Rachel M. Starkov, Pavel Sheppard, Tom D. J Org Chem [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. American Chemical Society 2013-04-16 2013-05-03 /pmc/articles/PMC3671500/ /pubmed/23586467 http://dx.doi.org/10.1021/jo400509n Text en Copyright © 2013 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Lanigan, Rachel M.
Starkov, Pavel
Sheppard, Tom D.
Direct Synthesis of Amides from Carboxylic Acids and Amines Using B(OCH(2)CF(3))(3)
title Direct Synthesis of Amides from Carboxylic Acids and Amines Using B(OCH(2)CF(3))(3)
title_full Direct Synthesis of Amides from Carboxylic Acids and Amines Using B(OCH(2)CF(3))(3)
title_fullStr Direct Synthesis of Amides from Carboxylic Acids and Amines Using B(OCH(2)CF(3))(3)
title_full_unstemmed Direct Synthesis of Amides from Carboxylic Acids and Amines Using B(OCH(2)CF(3))(3)
title_short Direct Synthesis of Amides from Carboxylic Acids and Amines Using B(OCH(2)CF(3))(3)
title_sort direct synthesis of amides from carboxylic acids and amines using b(och(2)cf(3))(3)
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3671500/
https://www.ncbi.nlm.nih.gov/pubmed/23586467
http://dx.doi.org/10.1021/jo400509n
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