Radical ring opening reaction of pyridine fused heterocycles with IBA-N3 catalyzed by tetra-n-butylammonium iodide

• Published in: Tetrahedron Vol. 75; no. 15; pp. 2298 - 2305
• Main Authors: Wang, Ruonan, Wang, Shiwei, Li, Dayong, Ye, Feiyang, Leng, Yuting, Wu, Yangjie, Chang, Junbiao, Wu, Yusheng
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 12.04.2019; Elsevier
• Subjects: Chemistry; Chemistry, Organic; IBA-N3; Physical Sciences; Pyridine fused heterocycles; Ring opening reaction; Science & Technology; Ring opening reaction; IBA-N3; Pyridine fused heterocycles; MILD; ALPHA-IMINONITRILES; ALKENES; AZIDATION; ACIDS; CHEMISTRY; CYANATION; STABLE AZIDOIODINANES; ACCESS; IBA-N-3
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2019.02.061

A mild, metal-free and efficient synthesis of 2,3-disubstituted acrylonitriles and α-iminonitriles through radical ring opening reaction of pyridine fused heterocycles has been developed. The tetra-n-butylammonium iodide catalyst acts as a formal one-electron donor. Compared to the previous methods, which require excessive amounts of highly explosive azide sources and the addition of oxidants, this is a safe and convenient transformation. [Display omitted] •Radical ring opening reaction of pyridine fused heterocycles with IBA-N3.•The synthesis of acrylonitriles and α-iminonitriles at room temperature.•Clean reaction, ease of product isolation and a simple experimental procedure.