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J Org Chem. 2000 Dec 15;65(25):8763-6.

A facile synthesis of perfluoroalkyl vinyl iodides and their palladium-mediated cross-coupling reactions.

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  • 1Herbert C. Brown Center for Borane Research, Department of Chemistry, Purdue University, West Lafayette, Indiana 47907-1393, USA.


Catalytic amounts of zinc, as low as 10 mol %, in the presence of trifluoroacetic acid (TFA) initiate the radical addition of perfluoroalkyl iodides to terminal alkynes with high regio- and stereoselectivities. Palladium-mediated cross-coupling of these (E)-perfluoroalkyl vinyl iodides allows for a facile synthesis of potentially useful fluoroorganic intermediates.

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