Talbot EP. A, * Fernandes Tde A, McKenna JM, * Toste FD. * Novartis Institutes for
Biomedical Research, Horsham, UK; University of California, Berkeley, USA
Asymmetric Palladium-Catalyzed Directed Intermolecular Fluoroarylation of Styrens.
J. Am. Chem. Soc. 2014;
136: 4101-4104
Key words
fluoroarylation - styrenes - palladium
Significance
The authors developed a highly enantioselective palladium-catalyzed fluoroarylation
of styrenes bearing an amide-based directing group. The proposed reaction mechanism
involves a palladium(IV) intermediate as shown above.
Comment
In this reaction, N,N-ligands play a crucial role to afford the fluoroarylated products.
Without these ligands only Heck products were obtained. Organic phosphate was added
as phase-transfer catalyst to increase the chemical yield.
