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Synfacts 2014; 10(6): 0617
DOI: 10.1055/s-0033-1339002
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Fluoroarylation Catalyzed by Palladium

Contributor(s):
Hisashi Yamamoto
,
Yasushi Shimoda
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
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Further Information

Publication History

Publication Date:
16 May 2014 (online)

 
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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.


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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.


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