Tailored Ligand Acceleration of the Cu-Catalyzed Azide−Alkyne Cycloaddition Reaction: Practical and Mechanistic Implications

• Published in: Journal of the American Chemical Society Vol. 132; no. 41; pp. 14570 - 14576
• Main Authors: Presolski, Stanislav I, Hong, Vu, Cho, So-Hye, Finn, M.G
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 20.10.2010
• Subjects: Alkynes - chemistry; Azides - chemistry; Catalysis; Copper - chemistry; Cyclization; Kinetics; Ligands; Solvents
• ISSN: 0002-7863; 1520-5126; 1520-5126
• DOI: 10.1021/ja105743g

Tris(heterocyclemethyl)amines containing mixtures of 1,2,3-triazolyl, 2-benzimidazoyl, and 2-pyridyl components were prepared for ligand acceleration of the copper-catalyzed azide−alkyne cycloaddition reaction. Two classes of ligands were identified: those that give rise to high reaction rates in co...