Palladium-catalyzed hydroarylation of alkynes with arenediazonium salts.

Org Lett

Dipartimento di Studi di Chimica e Tecnologia delle Sostanze Biologicamente Attive, Università degli Studi La Sapienza, Piazzale A. Moro 5, 00185 Rome, Italy.

Published: April 2008

The palladium-catalyzed hydroarylation of arenediazonium tetrafluoroborates with alkynes in the presence of triphenylsilane affords stereoselectively hydroarylation products in moderate to high yields. The reaction tolerates a variety of substituents including keto, ester, cyano, and nitro groups and can be performed as a one-pot procedure generating the arenediazonium salt in situ. With ethyl phenylpropynoate as the starting alkyne, the hydroarylation affords ethyl (Z)-2-arylcinnamates stereo- and regioselectively.

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http://dx.doi.org/10.1021/ol800266eDOI Listing

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