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Indexed by:期刊论文

Date of Publication:2019-02-01

Journal:ADVANCED SYNTHESIS & CATALYSIS

Included Journals:SCIE、Scopus

Volume:361

Issue:3

Page Number:469-475

ISSN No.:1615-4150

Key Words:5-trifluoromethylthio-1,2,3-triazoles; 5-thio-1,2,3-triazoles; rhodium; regioselectivity; mild conditions

Abstract: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.