N,N-Diethylurea-Catalyzed Amidation between Electron-Deficient Aryl Azides and Phenylacetaldehydes
Publication type: Journal Article
Publication date: 2015-01-23
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
25616121
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
Urea structures, of which N,N-diethylurea (DEU) proved to be the most efficient, were discovered to catalyze amidation reactions between electron-deficient aryl azides and phenylacetaldehydes. Experimental data support 1,3-dipolar cycloaddition between DEU-activated enols and electrophilic phenyl azides, especially perfluoroaryl azides, followed by rearrangement of the triazoline intermediate. The activation of the aldehyde under near-neutral conditions was of special importance in inhibiting dehydration/aromatization of the triazoline intermediate, thus promoting the rearrangement to form aryl amides.
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Metrics
31
Total citations:
31
Citations from 2024:
3
(9.68%)
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GOST
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Xie S. et al. N,N-Diethylurea-Catalyzed Amidation between Electron-Deficient Aryl Azides and Phenylacetaldehydes // Organic Letters. 2015. Vol. 17. No. 3. pp. 636-639.
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Xie S., Ramström O., Yan M. N,N-Diethylurea-Catalyzed Amidation between Electron-Deficient Aryl Azides and Phenylacetaldehydes // Organic Letters. 2015. Vol. 17. No. 3. pp. 636-639.
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RIS
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TY - JOUR
DO - 10.1021/ol503655a
UR - https://doi.org/10.1021/ol503655a
TI - N,N-Diethylurea-Catalyzed Amidation between Electron-Deficient Aryl Azides and Phenylacetaldehydes
T2 - Organic Letters
AU - Xie, Sheng
AU - Ramström, Olof
AU - Yan, Mingdi
PY - 2015
DA - 2015/01/23
PB - American Chemical Society (ACS)
SP - 636-639
IS - 3
VL - 17
PMID - 25616121
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (up to 50 authors)
Copy
@article{2015_Xie,
author = {Sheng Xie and Olof Ramström and Mingdi Yan},
title = {N,N-Diethylurea-Catalyzed Amidation between Electron-Deficient Aryl Azides and Phenylacetaldehydes},
journal = {Organic Letters},
year = {2015},
volume = {17},
publisher = {American Chemical Society (ACS)},
month = {jan},
url = {https://doi.org/10.1021/ol503655a},
number = {3},
pages = {636--639},
doi = {10.1021/ol503655a}
}
Cite this
MLA
Copy
Xie, Sheng, et al. “N,N-Diethylurea-Catalyzed Amidation between Electron-Deficient Aryl Azides and Phenylacetaldehydes.” Organic Letters, vol. 17, no. 3, Jan. 2015, pp. 636-639. https://doi.org/10.1021/ol503655a.