Advanced Synthesis & Catalysis · 2019 · 34 citations · 49 references
Natural SciencesChemistryCatalysisOrganic ChemistryOrganometallic ChemistryHeterocycle SynthesisHeterocyclic ChemistryCopper-catalyzed CouplingTriazole Chemistry
Abstract Copper‐catalyzed coupling of π‐deficient NH‐azoles with vinylboronic acids or vinyltrifluoroborate salt provides a direct route to N2 ‐vinyl‐1,2,3‐triazoles and N2 ‐vinyltetrazoles. The coupling reaction is efficiently catalyzed by (phen)Cu(PPh 3 )Br with low catalyst loading (5 mol%) under base‐free conditions. The method is applicable for vinylation of unsubstituted, monosubstituted, and disubstituted 1,2,3‐triazoles with various functionalities with high N2 ‐selectivity. magnified image
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Scott D. McCann, Shannon S. Stahl · Accounts of Chemical Research · 2015 · 542 citations · Full text