期刊
ORGANOMETALLICS
卷 31, 期 13, 页码 4904-4915出版社
AMER CHEMICAL SOC
DOI: 10.1021/om300513w
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资金
- Hong Kong Research Grant Council [HKUST 601306, HKUST 601408, HKU1/CRF/08]
- National Natural Science Foundation of China [21172069, 21190033]
- Shanghai Municipal Education Commission [12ZZ050]
- Fundamental Research Funds for the Central Universities
The catalytic activity of a series of ruthenium complexes lacking cyclopentadienyl ligands has been evaluated for the cycloaddition of terminal alkynes and azides to give selectively 1,4-disubstituted 1,2,3-triazoles. The complex RuH(eta(2)-BH4)(CO)(PCy3)(2) was found to be an effective catalyst for the cycloaddition reactions. In the presence of RuH(eta(2)-BH4)(CO)(PCy3)(2), primary and secondary azides reacted with a range of terminal alkynes containing various functionalities to selectively produce 1,4-disubstituted 1,2,3-triazoles. The ruthenium-catalyzed azide-alkyne cycloaddition appears to proceed via a Ru-acetylide species as the key intermediate, which undergoes formal cycloaddition with an azide to give a ruthenium triazolide complex. The 1,4-disubstituted 1,2,3-triazole product is generated by metathesis of the triazolide complex with a terminal alkyne. In support of the reaction mechanism, the acetylide complex Ru(C CCMe3)(2)(CO)(PPh3)(3) reacts cleanly with benzyl azide to give a ruthenium triazolide complex, which reacts with excess tert-butylacetylene in the presence of PPh3 to give 4-tert-butyl-1-benzyl-1,2,3-triazole and the diacetylide complex Ru(C CCMe3)(2)(CO)(PPh3)(3). The mechanism is also supported by DFT calculations.
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