Release Time:2019-10-10  Hits:

Indexed by: Journal Article

Date of Publication: 2019-02-01

Journal: ADVANCED SYNTHESIS & CATALYSIS

Included Journals: Scopus、SCIE

Volume: 361

Issue: 3

Page Number: 469-475

ISSN: 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.