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Single‐Flask Multicomponent Palladium‐Catalyzed α,γ‐Coupling of Ketone Enolates: Facile Preparation of Complex Carbon Scaffolds
Author(s) -
Grigalunas Michael,
Norrby PerOla,
Wiest Olaf,
Helquist Paul
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201505895
Subject(s) - palladium , ketone , catalysis , chemistry , coupling reaction , combinatorial chemistry , coupling (piping) , palladium catalyst , carbon fibers , organic chemistry , polymer chemistry , materials science , composite number , metallurgy , composite material
Abstract 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.