Tetramethyl orthosilicate (TMOS) as a reagent for direct amidation of carboxylic acids
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Supporting information
Author(s)
Type
Journal Article
Abstract
Tetramethyl orthosilicate (TMOS) is shown to be an effective reagent for direct amidation of aliphatic and aromatic carboxylic acids with amines and anilines. The amide products are obtained in good to quantitative yields in pure form directly after workup without the need for any further purification. A silyl ester as the putative activated intermediate is observed by NMR methods. Amidations on a 1 mol scale are demonstrated with a favorable process mass intensity.
Date Issued
2018-02-02
Date Acceptance
2018-01-30
Citation
Organic Letters, 2018, 20 (4), pp.950-953
ISSN
1523-7052
Publisher
American Chemical Society
Start Page
950
End Page
953
Journal / Book Title
Organic Letters
Volume
20
Issue
4
Copyright Statement
This is an open access article published under a Creative Commons Attribution (CC-BY)
License, which permits unrestricted use, distribution and reproduction in any medium,
provided the author and source are cited.
License, which permits unrestricted use, distribution and reproduction in any medium,
provided the author and source are cited.
License URL
Sponsor
Engineering & Physical Science Research Council (EPSRC)
Identifier
https://pubs.acs.org/doi/10.1021/acs.orglett.7b03841
Grant Number
EP/P030742/1
Subjects
Science & Technology
Physical Sciences
Chemistry, Organic
Chemistry
AMIDE BOND FORMATION
CATALYZED DIRECT AMIDATION
ROOM-TEMPERATURE
MESOPOROUS SILICA
PEPTIDE-SYNTHESIS
COUPLING REAGENT
CONVENIENT METHOD
AMINO-ACIDS
IN-SITU
CARBOXAMIDES
Organic Chemistry
03 Chemical Sciences
Publication Status
Published
Date Publish Online
2018-02-02