Synthesis of Multisubstituted 1,2,3-Triazoles: Regioselective Formation and Reaction Mechanism
Tzu-Ching Chi
1
,
Po-Chun Yang
1
,
Shao-Kung Hung
1
,
Shao-Kang Hung
1
,
Hui-Wen Wu
1
,
Hui Wen Wu
1
,
Hong-Chi Wang
1
,
Hsin-Kuan Liu
2
,
Hsin Kuan Liu
2
,
Li-Wen Liu
3
,
Ho Hsuan Chou
1
3
National Tainan First Senior High School, Tainan 701, Taiwan
|
Publication type: Journal Article
Publication date: 2024-03-28
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
38546539
Organic Chemistry
Abstract
A synthetically useful approach to functionalized triazoles is described via the reaction of β-carbonyl phosphonates and azides. 1,4- and 1,5-disubstituted and 1,4,5-trisubstituted triazoles can be regio- and chemoselectively accessed under mild conditions in good to excellent yields (31 examples, up to 99%). A mechanism is proposed that rationalizes the avoidance of the 4-phosphonate byproducts, which is aligned with crystallographic and experimental evidence.
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16
Total citations:
16
Citations from 2024:
16
(100%)
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MLA
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GOST
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Chi T. et al. Synthesis of Multisubstituted 1,2,3-Triazoles: Regioselective Formation and Reaction Mechanism // Journal of Organic Chemistry. 2024. Vol. 89. No. 8. pp. 5401-5408.
GOST all authors (up to 50)
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Chi T., Yang P., Hung S., Hung S., Wu H., Wu H. W., Wang H., Liu H., Liu H. K., Liu L., Chou H. H. Synthesis of Multisubstituted 1,2,3-Triazoles: Regioselective Formation and Reaction Mechanism // Journal of Organic Chemistry. 2024. Vol. 89. No. 8. pp. 5401-5408.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.joc.3c02836
UR - https://pubs.acs.org/doi/10.1021/acs.joc.3c02836
TI - Synthesis of Multisubstituted 1,2,3-Triazoles: Regioselective Formation and Reaction Mechanism
T2 - Journal of Organic Chemistry
AU - Chi, Tzu-Ching
AU - Yang, Po-Chun
AU - Hung, Shao-Kung
AU - Hung, Shao-Kang
AU - Wu, Hui-Wen
AU - Wu, Hui Wen
AU - Wang, Hong-Chi
AU - Liu, Hsin-Kuan
AU - Liu, Hsin Kuan
AU - Liu, Li-Wen
AU - Chou, Ho Hsuan
PY - 2024
DA - 2024/03/28
PB - American Chemical Society (ACS)
SP - 5401-5408
IS - 8
VL - 89
PMID - 38546539
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2024_Chi,
author = {Tzu-Ching Chi and Po-Chun Yang and Shao-Kung Hung and Shao-Kang Hung and Hui-Wen Wu and Hui Wen Wu and Hong-Chi Wang and Hsin-Kuan Liu and Hsin Kuan Liu and Li-Wen Liu and Ho Hsuan Chou},
title = {Synthesis of Multisubstituted 1,2,3-Triazoles: Regioselective Formation and Reaction Mechanism},
journal = {Journal of Organic Chemistry},
year = {2024},
volume = {89},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://pubs.acs.org/doi/10.1021/acs.joc.3c02836},
number = {8},
pages = {5401--5408},
doi = {10.1021/acs.joc.3c02836}
}
Cite this
MLA
Copy
Chi, Tzu-Ching, et al. “Synthesis of Multisubstituted 1,2,3-Triazoles: Regioselective Formation and Reaction Mechanism.” Journal of Organic Chemistry, vol. 89, no. 8, Mar. 2024, pp. 5401-5408. https://pubs.acs.org/doi/10.1021/acs.joc.3c02836.