Redox‐Neutral Metal‐Free Three‐Component Carbonylative Dearomatization of Pyridine Derivatives with CO2. Issue 67 (7th November 2019)

• Record Type: Journal Article
• Authors: Cerveri, Alessandro; Pace, Stefano; Monari, Magda; Lombardo, Marco; Bandini, Marco
• Is Part Of: Chemistry. Volume 25:Issue 67(2019)
• Page Start: 15272
• Page End: 15276
• Publication Date: 2019-11-07
• Subjects: carbonylation -- CO2 -- dearomatization reaction -- metal-free -- pyridine; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201904359
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: The TBD (1, 3, 5‐triazabicyclodec‐5‐ene) assisted three‐component carbonylation of pyridine‐2‐methanamines is documented by means of CO2 as a benign CO surrogate. The redox‐neutral methodology enables the realization of densely functionalized imidazo‐pyridinones in high yields (up to 93 %) and excellent chemoselectivity. Combined computational and experimental investigations revealed an unprecedented RCOCl/TBD concerted electrophilic activation of carbon dioxide. Abstract : Three is better than two ! A three‐component metal‐free carbonylative dearomatization of pyridine derivatives is documented with CO2 as a CO surrogate. A range of imidazo‐pyridinones are obtained in high yield (up to 93 %) through an unprecedented RCOCl/TBD concerted electrophilic activation of carbon dioxide (see scheme).