1428318-79-9

Upstream product

• 1428318-58-4 1-benzyl-5-fluoro-4-phenyl-1H-1,2,3-triazole 
• 100-53-8 phenylmethanethiol 
• 150-60-7 dibenzyl disulphide 
• 100-39-0 benzyl bromide 
• 92497-27-3 (toluenesulfanyl)phenylacetylene 
• 622-79-7 benzyl azide 
• 1589-82-8 phenylmagnesium bromide 
• 83893-97-4 (thiocyanatoethynyl)benzene 
• 536-74-3 phenylacetylene 
• 860002-66-0 1-benzyl-4-phenyl-5-iodo-1,2,3-triazole 

Relevant academic research and scientific papers

Chemo- And regioselective click reactions through nickel-catalyzed azide-alkyne cycloaddition

Metal-catalyzed cycloaddition is an expeditious synthetic route to functionalized heterocyclic frameworks. However, achieving reactivity-controlled metal-catalyzed azide-alkyne cycloadditions from competing internal alkynes has been challenging. Herein, we report a nickel-catalyzed [3 + 2] cycloaddition of unsymmetrical alkynes with organic azides to afford functionalized 1,2,3-triazoles with excellent regio- and chemoselectivity control. Terminal alkynes and cyanoalkynes afford 1,5-disubstituted triazoles and 1,4,5-trisubstituted triazoles bearing a 4-cyano substituent, respectively. Thioalkynes and ynamides exhibit inverse regioselectivity compared with terminal alkynes and cyanoalkynes, affording 1,4,5-trisubstituted triazoles with 5-thiol and 5-amide substituents, respectively. Density functional theory calculations are performed for the elucidation of the reaction mechanism. The computed mechanism suggests that a nickellacyclopropene intermediate is generated by the oxidative addition of the alkyne substrate to the Ni(0)-Xantphos catalyst, and the subsequent C-N coupling of this intermediate with an azide is responsible for the chemo- and regioselectivity.

Ruthenium-Catalyzed Highly Regioselective Azide-Internal Thiocyanatoalkyne Cycloaddition under Mild Conditions: Experimental and Theoretical Studies

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).

Halogen exchange (Halex) reaction of 5-iodo-1,2,3-triazoles: Synthesis and applications of 5-fluorotriazoles

A good exchange: 5-Iodo-1,2,3-triazoles undergo facile substitution reactions with fluoride salts, thus providing ready access to 5-fluorotriazoles (see scheme). The latter can be further elaborated with various nucleophiles to furnish fully substituted 1,2,3-triazole compounds. Copyright