Palladium-catalyzed hydroarylation of propiolamides. A regio-and stereocontrolled method for preparing 3, 3-diarylacrylamides

LA Hay, TM Koenig, FO Ginah, JD Copp…

Index: Hay, Lynne A.; Koenig, Thomas M.; Ginah, Francis O.; Copp, James D.; Mitchell, David Journal of Organic Chemistry, 1998 , vol. 63, # 15 p. 5050 - 5058

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Citation Number: 54

Abstract

A general regio-and stereoselective synthesis of 3, 3-diarylacrylamides is reported. Palladium-catalyzed coupling reactions of propiolamides with aryl halides provide arylpropiolamides. A subsequent hydroarylation reaction of these arylpropiolamides with aryl halides, catalytic palladium, an amine base, and formic acid in refluxing ethyl acetate provides 3, 3-diarylacrylamides regio-and stereoselectively. The unique stereo-and ...