Silver-Catalyzed Decarboxylative Radical Azidation of Aliphatic Carboxylic Acids in Aqueous Solution
Publication type: Journal Article
Publication date: 2015-07-30
scimago Q1
wos Q1
SJR: 5.554
CiteScore: 22.5
Impact factor: 15.6
ISSN: 00027863, 15205126
PubMed ID:
26217910
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
We report herein an efficient and general method for the decarboxylative azidation of aliphatic carboxylic acids. Thus, with AgNO3 as the catalyst and K2S2O8 as the oxidant, the reactions of various aliphatic carboxylic acids with tosyl azide or pyridine-3-sulfonyl azide in aqueous CH3CN solution afforded the corresponding alkyl azides under mild conditions. A broad substrate scope and wide functional group compatibility were observed. A radical mechanism is proposed for this site-specific azidation.
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Metrics
182
Total citations:
182
Citations from 2024:
23
(12%)
Cite this
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MLA
Cite this
GOST
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Liu C. et al. Silver-Catalyzed Decarboxylative Radical Azidation of Aliphatic Carboxylic Acids in Aqueous Solution // Journal of the American Chemical Society. 2015. Vol. 137. No. 31. pp. 9820-9823.
GOST all authors (up to 50)
Copy
Liu C., Wang X., Li Z., Cui L., Li C. Silver-Catalyzed Decarboxylative Radical Azidation of Aliphatic Carboxylic Acids in Aqueous Solution // Journal of the American Chemical Society. 2015. Vol. 137. No. 31. pp. 9820-9823.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/jacs.5b06821
UR - https://doi.org/10.1021/jacs.5b06821
TI - Silver-Catalyzed Decarboxylative Radical Azidation of Aliphatic Carboxylic Acids in Aqueous Solution
T2 - Journal of the American Chemical Society
AU - Liu, Chao
AU - Wang, Xiaoqing
AU - Li, Zhaodong
AU - Cui, Lei
AU - Li, Chaozhong
PY - 2015
DA - 2015/07/30
PB - American Chemical Society (ACS)
SP - 9820-9823
IS - 31
VL - 137
PMID - 26217910
SN - 0002-7863
SN - 1520-5126
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2015_Liu,
author = {Chao Liu and Xiaoqing Wang and Zhaodong Li and Lei Cui and Chaozhong Li},
title = {Silver-Catalyzed Decarboxylative Radical Azidation of Aliphatic Carboxylic Acids in Aqueous Solution},
journal = {Journal of the American Chemical Society},
year = {2015},
volume = {137},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/jacs.5b06821},
number = {31},
pages = {9820--9823},
doi = {10.1021/jacs.5b06821}
}
Cite this
MLA
Copy
Liu, Chao, et al. “Silver-Catalyzed Decarboxylative Radical Azidation of Aliphatic Carboxylic Acids in Aqueous Solution.” Journal of the American Chemical Society, vol. 137, no. 31, Jul. 2015, pp. 9820-9823. https://doi.org/10.1021/jacs.5b06821.