Triphenylphosphine Sulfide as an Efficient Ligand in CuAAC to Synthesize 4-Phosphinyl-1,2,3-Triazoles
- 1State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China
- 2Department of Applied Chemistry, Okayama University of Science, 1-1 Ridai-cho, Kita-ku, Okayama 700-0005, Japan
Abstract
Triphenylphosphine sulfide ligand (L1) exhibited excellent catalytic performance in the copper-catalyzed azide–alkyne cycloaddition (CuAAC) of ethynyldiphenylphosphine oxide (1) and azides (2), affording functionalized 4-phosphinyl-1,2,3-triazoles (3) in good yields. L1 showed superior performance to triphenylphosphine oxide, triphenylphosphine, and the sulfide ligands examined, possibly owing to suitable coordination of its P=S moiety to Cu. And, the products could be transformed to 4-phosphanyl-1,2,3-triazoles (4) and 1-benzyl-substituted 1,2,3-triazoles (5) by reduction and dephosphinylation, respectively. This [Cu]/L1-catalyzed protocol, the first example of the application of triphenylphosphine sulfide as a ligand in CuAAC, featured the following advantages: low catalyst loading, relatively short reaction time, broad functional group tolerance, high yields, and facile scalability.
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BibTeX
@article{shen2026triphenylphosphine,
title = {{Triphenylphosphine Sulfide as an Efficient Ligand in CuAAC to Synthesize 4-Phosphinyl-1,2,3-Triazoles}},
author = {Jie Shen and Jinwei Li and Shitang Xu and Yasuhiro Okuda and Zetao Jiang and Bingting Yao and Hui Li and Yinchun Jiao and Zilong Tang and Lifen Peng and Akihiro Orita and Xinhua Xu},
journal = {Molecules},
year = {2026},
month = nov,
doi = {10.3390/molecules31214005},
url = {https://www.mdpi.com/1420-3049/31/21/4005},
note = {CC BY 4.0},
}
RIS
TY - JOUR
TI - Triphenylphosphine Sulfide as an Efficient Ligand in CuAAC to Synthesize 4-Phosphinyl-1,2,3-Triazoles
AU - Jie Shen
AU - Jinwei Li
AU - Shitang Xu
AU - Yasuhiro Okuda
AU - Zetao Jiang
AU - Bingting Yao
AU - Hui Li
AU - Yinchun Jiao
AU - Zilong Tang
AU - Lifen Peng
AU - Akihiro Orita
AU - Xinhua Xu
PY - 2026
DA - 2026/11/06
JO - Molecules
DO - 10.3390/molecules31214005
UR - https://www.mdpi.com/1420-3049/31/21/4005
AB - Triphenylphosphine sulfide ligand (L1) exhibited excellent catalytic performance in the copper-catalyzed azide–alkyne cycloaddition (CuAAC) of ethynyldiphenylphosphine oxide (1) and azides (2), affording functionalized 4-phosphinyl-1,2,3-triazoles (3) in good yields. L1 showed superior performance to triphenylphosphine oxide, triphenylphosphine, and the sulfide ligands examined, possibly owing to suitable coordination of its P=S moiety to Cu. And, the products could be transformed to 4-phosphanyl-1,2,3-triazoles (4) and 1-benzyl-substituted 1,2,3-triazoles (5) by reduction and dephosphinylation, respectively. This [Cu]/L1-catalyzed protocol, the first example of the application of triphenylphosphine sulfide as a ligand in CuAAC, featured the following advantages: low catalyst loading, relatively short reaction time, broad functional group tolerance, high yields, and facile scalability.
SN - 1420-3049
ER -