Release Time:2020-02-12  Hits:

Indexed by: Journal Papers

Date of Publication: 2019-11-19

Journal: ADVANCED SYNTHESIS & CATALYSIS

Included Journals: SCIE

Volume: 361

Issue: 22

Page Number: 5258-5263

ISSN: 1615-4150

Key Words: 5-Thiocyanato-1; 2; 3-triazoles; Triazolyl-organosulfurs; Cascade reaction; Internal thiocyanatoalkynes

Abstract: Fully substituted heterofunctionalized triazoles can be prepared by indirect and direct approaches. The indirect strategies are well-established but have limitations. Herein, we developed a direct methodology to access fully substituted 5-thiocyanato-1,2,3-triazoles with high regioselectivity from the azide-internal thiocyanatoalkyne cycloaddition reaction under mild conditions. This is the first time that fully substituted 5-thiocyanato-1,2,3-triazoles have been prepared and the first time an AAC/nucleophilic substitution cascade reaction have been used to generate various fully substituted triazolyl-organosulfurs, such as 5-sulfur-triazoles and 5-sulfinylcyanato-triazoles from common internal thiocyanatoalkyne precursors. This approach features a broad substrate scope (34 examples), good compatibility with water and air, high yields (up to 85%) and excellent regioselectivity (more than 20:1).