Copper-Catalyzed Coupling of Pyridines and Quinolines with Alkynes:  A One-Step, Asymmetric Route to Functionalized Heterocycles

• Published in: Journal of organic chemistry Vol. 73; no. 5; pp. 1906 - 1910
• Main Authors: Black, Daniel A, Beveridge, Ramsay E, Arndtsen, Bruce A
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 07-03-2008
• Subjects: Chemistry; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Organic chemistry; Preparations and properties; Catalytic reaction; Isoquinoline derivatives; Acetylenic compound; Nitrogen heterocycle; Quinoline derivatives; Organic carbamate; Pyridine derivatives; Copper ion; Functionalization; Asymmetric synthesis; Cross reaction; Copper I; Chemical synthesis; Alkyne; Nucleophile
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo702293h

A copper (I)-catalyzed, asymmetric method to directly functionalize pyridines, quinolines, and isoquinolines with terminal alkynes is described. The reaction is readily diversified to incorporate a range of pyridine-based heterocycles and electron-rich or electron-poor alkynes. This provides a straightforward alternative to nucleophilic or cross-coupling approaches to directly derivatize these heterocycles, and yields useful propargylcarbamates.