Organic Letters, volume 17, issue 3, pages 636-639
N,N-Diethylurea-Catalyzed Amidation between Electron-Deficient Aryl Azides and Phenylacetaldehydes
1
2
Department
of Chemistry, University of Massachusetts Lowell, 1 University
Ave., Lowell, Massachusetts 01854, United States
|
Publication type: Journal Article
Publication date: 2015-01-23
Journal:
Organic Letters
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 5.2
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.
Top-30
Citations by journals
|
1
2
3
|
|
|
Journal of Organic Chemistry
3 publications, 9.68%
|
|
|
Journal of Fluorine Chemistry
2 publications, 6.45%
|
|
|
Macromolecules
2 publications, 6.45%
|
|
|
RSC Advances
2 publications, 6.45%
|
|
|
New Journal of Chemistry
2 publications, 6.45%
|
|
|
Current Organic Chemistry
1 publication, 3.23%
|
|
|
Molecules
1 publication, 3.23%
|
|
|
Tetrahedron Letters
1 publication, 3.23%
|
|
|
Journal of Colloid and Interface Science
1 publication, 3.23%
|
|
|
ChemInform
1 publication, 3.23%
|
|
|
Advanced Synthesis and Catalysis
1 publication, 3.23%
|
|
|
European Journal of Organic Chemistry
1 publication, 3.23%
|
|
|
Angewandte Chemie - International Edition
1 publication, 3.23%
|
|
|
Angewandte Chemie
1 publication, 3.23%
|
|
|
Chemistry - An Asian Journal
1 publication, 3.23%
|
|
|
ACS applied materials & interfaces
1 publication, 3.23%
|
|
|
Accounts of Chemical Research
1 publication, 3.23%
|
|
|
Chemical Science
1 publication, 3.23%
|
|
|
Green Chemistry
1 publication, 3.23%
|
|
|
Materials Chemistry Frontiers
1 publication, 3.23%
|
|
|
Synthetic Communications
1 publication, 3.23%
|
|
|
Proceedings of the National Academy of Sciences of the United States of America
1 publication, 3.23%
|
|
|
Synlett
1 publication, 3.23%
|
|
|
Russian Chemical Reviews
1 publication, 3.23%
|
|
|
1
2
3
|
Citations by publishers
|
1
2
3
4
5
6
7
|
|
|
American Chemical Society (ACS)
7 publications, 22.58%
|
|
|
Royal Society of Chemistry (RSC)
7 publications, 22.58%
|
|
|
Wiley
6 publications, 19.35%
|
|
|
Elsevier
4 publications, 12.9%
|
|
|
Bentham Science
1 publication, 3.23%
|
|
|
Multidisciplinary Digital Publishing Institute (MDPI)
1 publication, 3.23%
|
|
|
Taylor & Francis
1 publication, 3.23%
|
|
|
Proceedings of the National Academy of Sciences (PNAS)
1 publication, 3.23%
|
|
|
Thieme
1 publication, 3.23%
|
|
|
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 3.23%
|
|
|
1
2
3
4
5
6
7
|
- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
{"yearsCitations":{"type":"bar","data":{"show":true,"labels":[2015,2016,2017,2018,2019,2020,2021,2022,2023,2024],"ids":[0,0,0,0,0,0,0,0,0,0],"codes":[0,0,0,0,0,0,0,0,0,0],"imageUrls":["","","","","","","","","",""],"datasets":[{"label":"Citations number","data":[3,5,8,2,5,2,1,2,0,3],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":["9.68","16.13","25.81","6.45","16.13","6.45","3.23","6.45",0,"9.68"],"barThickness":null}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"journals":{"type":"bar","data":{"show":true,"labels":["Journal of Organic Chemistry","Journal of Fluorine Chemistry","Macromolecules","RSC Advances","New Journal of Chemistry","Current Organic Chemistry","Molecules","Tetrahedron Letters","Journal of Colloid and Interface Science","ChemInform","Advanced Synthesis and Catalysis","European Journal of Organic Chemistry","Angewandte Chemie - International Edition","Angewandte Chemie","Chemistry - An Asian Journal","ACS applied materials & interfaces","Accounts of Chemical Research","Chemical Science","Green Chemistry","Materials Chemistry Frontiers","Synthetic Communications","Proceedings of the National Academy of Sciences of the United States of America","Synlett","Russian Chemical Reviews"],"ids":[8697,14755,20817,3100,1404,16175,1770,6133,24202,25372,3906,19472,19215,25450,10120,1458,1526,9646,1017,7063,1646,306,10217,23802],"codes":[0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/doUaFUZdxUEQjLi1TwZjGHi8HXYNWWSk04dSC6Xh_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/5YZtvLvkPZuc2JHOaZsjCvGSHFCuC3drUwN3YAc5_medium.webp","\/storage\/images\/resized\/mxFdPe9qujsfvfYfcN0QOclAiYORFb0xrRlwV8gs_medium.webp","\/storage\/images\/resized\/xqixcltwJYe6H8Uco2JbAFfIOzt7UNKH0OcPOPzO_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp"],"datasets":[{"label":"","data":[3,2,2,2,2,1,1,1,1,1,1,1,1,1,1,1,1,1,1,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[9.68,6.45,6.45,6.45,6.45,3.23,3.23,3.23,3.23,3.23,3.23,3.23,3.23,3.23,3.23,3.23,3.23,3.23,3.23,3.23,3.23,3.23,3.23,3.23],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Journals","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"publishers":{"type":"bar","data":{"show":true,"labels":["American Chemical Society (ACS)","Royal Society of Chemistry (RSC)","Wiley","Elsevier","Bentham Science","Multidisciplinary Digital Publishing Institute (MDPI)","Taylor & Francis","Proceedings of the National Academy of Sciences (PNAS)","Thieme","Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii"],"ids":[40,123,11,17,39,202,18,162,135,9422],"codes":[0,0,0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/doUaFUZdxUEQjLi1TwZjGHi8HXYNWWSk04dSC6Xh_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/5YZtvLvkPZuc2JHOaZsjCvGSHFCuC3drUwN3YAc5_medium.webp","\/storage\/images\/resized\/mxFdPe9qujsfvfYfcN0QOclAiYORFb0xrRlwV8gs_medium.webp","\/storage\/images\/resized\/xqixcltwJYe6H8Uco2JbAFfIOzt7UNKH0OcPOPzO_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp"],"datasets":[{"label":"","data":[7,7,6,4,1,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[22.58,22.58,19.35,12.9,3.23,3.23,3.23,3.23,3.23,3.23],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Publishers","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"yearsCitationsQuartiles":{"type":"bar","data":{"show":true,"labels":[2015,2016,2017,2018,2019,2020,2021,2022,2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0,0,0,0,0,0,0,0,0,0],"percentage":["0","0","0","0","0","0","0","0","0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[0,1,1,0,1,0,1,1,0,0],"percentage":["0","3.23","3.23","0","3.23","0","3.23","3.23","0","0"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[1,0,2,0,0,1,0,0,0,2],"percentage":["3.23","0","6.45","0","0","3.23","0","0","0","6.45"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[1,4,5,2,4,1,0,0,0,1],"percentage":["3.23","12.9","16.13","6.45","12.9","3.23","0","0","0","3.23"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[1,0,0,0,0,0,0,1,0,0],"percentage":["3.23","0","0","0","0","0","0","3.23","0","0"]}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations quartiles by SCImago per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"yearsCitationsQuartilesWs":{"type":"bar","data":{"show":true,"labels":[2015,2016,2017,2018,2019,2020,2021,2022,2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0,0,0,0,0,0,0,0,0,0],"percentage":["0","0","0","0","0","0","0","0","0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[0,1,1,0,1,0,1,0,0,1],"percentage":["0","3.23","3.23","0","3.23","0","3.23","0","0","3.23"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[1,0,2,0,2,1,0,1,0,1],"percentage":["3.23","0","6.45","0","6.45","3.23","0","3.23","0","3.23"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[1,4,4,2,2,1,0,0,0,1],"percentage":["3.23","12.9","12.9","6.45","6.45","3.23","0","0","0","3.23"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[1,0,1,0,0,0,0,1,0,0],"percentage":["3.23","0","3.23","0","0","0","0","3.23","0","0"]}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations quartiles by WoS per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}}}
Are you a researcher?
Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
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.
GOST all authors (up to 50)
Copy
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.
Cite this
RIS
Copy
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 00:00:00
PB - American Chemical Society (ACS)
SP - 636-639
IS - 3
VL - 17
PMID - 25616121
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex
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.