Single-Flask Multicomponent Palladium-Catalyzed α,γ-Coupling of Ketone Enolates: Facile Preparation of Complex Carbon Scaffolds.
A three-component palladium-catalyzed reaction sequence has been developed in which γ-substituted α,β-unsaturated products are obtained in a single flask by an α-alkenylation with either a subsequent γ-alkenylation or γ-arylation of a ketone enolate. Coupling of a variety of electronically and structurally different components was achieved in the presence of a Pd/Q-Phos catalyst (2 mol %), usually at 22 °C with yields of up to 85 %. Most importantly, access to these products is obtained in one simple operation in place of employing multiple reactions.
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556 (USA).
Michael
M
Grigalunas
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556 (USA).|Pharmaceutical Development, Global Medicines Development, AstraZeneca, 43183 Mölndal (Sweden).
Per-Ola
PO
Norrby
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556 (USA).|Lab of Computational Chemistry and Drug Design, School of Chemical Biology and Biotechnology, Peking University, Shenzhen Graduate School, Shenzhen 518055 (China).
Olaf
O
Wiest
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556 (USA). phelquis@nd.edu.
Paul
P
Helquist
cross-coupling; ketones; multicomponent reactions; palladium; synthetic methods