Lanigan, RM;
Starkov, P;
Sheppard, TD;
(2013)
Direct Synthesis of Amides from Carboxylic Acids and Amines Using B(OCH2CF3)3.
The Journal of Organic Chemistry
, 78
(9)
4512 - 4523.
10.1021/jo400509n.
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Abstract
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.
| Type: | Article |
|---|---|
| Title: | Direct Synthesis of Amides from Carboxylic Acids and Amines Using B(OCH2CF3)3 |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1021/jo400509n |
| Publisher version: | http://dx.doi.org/10.1021/jo400509n |
| Language: | English |
| Additional information: | This work is published under ACS AuthorChoice and is distributed under the Creative Commons Attribution CC-BY Licence. This license allows for redistribution and alteration, commercial and non-commercial, as long as credit is given to the author. To view a full copy of this license, visit: http://creativecommons.org/licenses |
| UCL classification: | UCL UCL > Provost and Vice Provost Offices > UCL BEAMS UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry |
| URI: | https://discovery.ucl.ac.uk/id/eprint/1392980 |
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