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Synfacts 2016; 12(11): 1181
DOI: 10.1055/s-0036-1589316
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Defluorinative Coupling of 1-Aryl-2,2-Difluoroalkenes and Boronic Acids

Contributor(s):
Paul Knochel
,
Marthe Ketels
Thornbury RT, Toste FD * University of California, Berkeley, USA
Palladium-Catalyzed Defluorinative Coupling of 1-Aryl-2,2-Difluoroalkenes and Boronic Acids: Stereoselective Synthesis of Monofluorostilbenes.

Angew. Chem. Int. Ed. 2016;
55: 11629-11632
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Publication History

Publication Date:
18 October 2016 (online)

 
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Key words

palladium catalysis - boronic acids - fluorine

Significance

The authors report a palladium-catalyzed defluorinative coupling of 1-aryl-2,2-difluoroalkenes with boronic acids with a broad functional-group tolerance, moderate yields and excellent diastereoselectivity.


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Comment

The utility of the reported method was demonstrated by the synthesis of a Gleevec® amide isostere.


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