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Redox‐Neutral Metal‐Free Three‐Component Carbonylative Dearomatization of Pyridine Derivatives with CO 2
Author(s) -
Cerveri Alessandro,
Pace Stefano,
Monari Magda,
Lombardo Marco,
Bandini Marco
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201904359
Subject(s) - carbonylation , chemoselectivity , pyridine , chemistry , electrophile , redox , combinatorial chemistry , carbon monoxide , metal , component (thermodynamics) , oxide , organic chemistry , catalysis , physics , thermodynamics
The TBD (1,3,5‐triazabicyclodec‐5‐ene) assisted three‐component carbonylation of pyridine‐2‐methanamines is documented by means of CO 2 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.