Redox-Neutral Metal-Free Three-Component Carbonylative Dearomatization of Pyridine Derivatives with CO2

Alessandro Cerveri; Stefano Pace; Magda Monari; Marco Lombardo; Marco Bandini

doi:10.1002/chem.201904359

Redox-Neutral Metal-Free Three-Component Carbonylative Dearomatization of Pyridine Derivatives with CO₂

Chemistry. 2019 Dec 2;25(67):15272-15276. doi: 10.1002/chem.201904359. Epub 2019 Nov 7.

Authors

Alessandro Cerveri¹, Stefano Pace¹, Magda Monari¹, Marco Lombardo¹, Marco Bandini¹

Affiliation

¹ Dipartimento di Chimica "G. Ciamician", Alma Mater Studiorum-Università di Bologna, via Selmi 2, 40126, Bologna, Italy.

PMID: 31553479
DOI: 10.1002/chem.201904359

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.

Keywords: CO2; carbonylation; dearomatization reaction; metal-free; pyridine.