Discovery of a Robust and Efficient Homogeneous Silver(I) Catalyst for the Cycloaddition of Azides onto Terminal Alkynes

• Published in: European journal of organic chemistry 2012-10, Vol.2012 (28), p.5462-5470
• Main Authors: McNulty, James, Keskar, Kunal
• Format: Article
• Language: English
• Subjects: Alk­ynes; Azides; Catalysis; Catalysts: preparations and properties; Chemistry; Click chemistry; Cycloaddition; Exact sciences and technology; General and physical chemistry; Heterocyclic compounds; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Ligands; Organic chemistry; Preparations and properties; Silver; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201200930

A highly efficient, chemically stable, and well‐defined homogeneous silver(I) catalyst is reported for the cycloaddition of azides onto terminal alkynes (Ag‐AAC reaction). The Ag‐AAC reaction occurs at room temperature or with heating to deliver exclusively the corresponding 1,4‐triazole. A pronounced ligand effect was discovered through systematic modification to the ligand structure resulting in the discovery of a chemically stable active catalyst for this reaction. A highly efficient, chemically stable, and well‐defined homogeneous silver(I) catalyst is reported for the cycloaddition of azides onto terminal alkynes (Ag‐AAC reaction).