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论文类型：期刊论文

发表时间：2019-02-01

发表刊物：ADVANCED SYNTHESIS & CATALYSIS

收录刊物：SCIE、Scopus

卷号：361

期号：3

页面范围：469-475

ISSN号：1615-4150

关键字：5-trifluoromethylthio-1,2,3-triazoles; 5-thio-1,2,3-triazoles; rhodium; regioselectivity; mild conditions

摘要：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.