ChemInform Abstract: Palladium-Catalyzed Hydroarylation of Propiolamides. A Regio- and Stereocontrolled Method for Preparing 3,3-Diarylacrylamides

Autor:	Thomas M. Koenig, David Mitchell, James Densmore Copp, Lynne A. Hay, Francis Orerenyo Ginah
Rok vydání:	2010
Předmět:	inorganic chemicals Chemistry Aryl Regioselectivity chemistry.chemical_element General Medicine Coupling reaction Catalysis chemistry.chemical_compound Amide Intramolecular force Organic chemistry Stereoselectivity Palladium
Zdroj:	ChemInform. 29
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.199850111
Popis:	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 regiocontrol is presumed to proceed through careful reaction parameters that allow intramolecular coordination of the propiolamide amide functionality to the transient palladium−alkyne complex. Palladium-catalyzed hydroarylation of propiolamides has not been studied; however, preliminary results from related systems suggest that regioselective addition can be achieved. The methodology as a synthesis tool is demonstrated in an efficient route to previously difficult-to-prepare potent, benzimidazole antiviral targets. In addition, the synthesis scope is explored where, by judicious c...
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::b57848727023b606443a7fd5594e7281 https://doi.org/10.1002/chin.199850111 Zobrazit plný text záznamu Plný text