期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 361, 期 3, 页码 469-475出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201801216
关键词
5-trifluoromethylthio-1,2,3-triazoles; 5-thio-1,2,3-triazoles; rhodium; regioselectivity; mild conditions
资金
- Doctoral Program Foundation of Liaoning Province [20170520378, 20170520274]
- Fundamental Research Funds for the Central Universities [DUT16RC(3)114, DUT18LK25]
- National Natural Science Foundation of China [21702025, 51703018]
A regioselective method to access fully substituted 5-trifluoromethylthio-1,2,3-triazoles and 5-thio-1,2,3-triazoles from the internal alkynyl trifluoromethyl sulfides and internal thioalkynes by a rhodium(I)-catalyzed azide-alkyne cycloaddition (RhAAC) reaction under mild conditions has been developed. This approach features good compatibility with water and air, a broad substrate scope, good functional group tolerance, high yields and excellent regioselectivities. The high 1,5-regioselectivities were controlled by the strong coordination between the sulfur atom and the pi-acidic rhodium. The advantages of this method further include its applicability to gram-scale preparation, the use of solid-phase synthesis technique, and the mutually orthogonal CuAAC-RhAAC reaction.
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