Palladium-Catalyzed Intermolecular Addition of Formamides to Alkynes
Tetsuaki Fujihara, Yuko Katafuchi, Tomohiro Iwai, Jun Terao and Yasushi Tsuji*
J. Am. Chem. Soc., DOI: 10.1021/ja910038p
A novel palladium system for an intermolecular addition of formamides to alkynes has been developed. The reaction of formamides with internal alkynes in the presence of a palladium catalyst with acid chloride as an additive afforded (E)-α,β-unsaturated amides regio- and stereoselectively. The same catalyst system realized the first example of the addition of formamides to terminal alkynes giving the corresponding α,β-unsaturated amides bearing a terminal methylene moiety as major products. The present reaction was widely applicable to substrates with various functionalities. This method also could be applied to the reaction of N,N-disubstituted formamides with norbornene. A hydridopalladium species would be formed as a key intermediate with in situ generated HCl under the reaction conditions.
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Date：2010/01/24(日) 17:26 ID：lpQTOCLP5U [ 返信 ]
