Selective unusual Pd-mediated biaryl coupling reactions: solvent effects with carbonate bases.
A one-step Pd-catalyzed reaction performed on an o-bromobenzamide permitted the selective formation of either phenanthridinones 2 via an ipso substitution or new phenanthridinone-1-carboxamides 3 through a direct N-arylation. A direct correlation between the solvent polarity and the carbonate base on the selectivity has been observed. The proposed catalytic cycle involves the initial formation of a common intermediate and depends on the base assistance.
Donati
Ludovic
L
Laboratoire de Pharmacognosie UMR CNRS 8638, Université Paris Descartes, 4 Avenue de l'Observatoire, F-75006 Paris, France.
Michel
Sylvie
S
Tillequin
François
F
Porée
François-Hugues
FH
D002254:Carbonates / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D010616:Phenanthrenes / Q000138:chemical synthesis* / Q000737:chemistry; D012997:Solvents / Q000737:chemistry
D002254:Carbonates; D010616:Phenanthrenes; D012997:Solvents; D010165:Palladium