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Palladium‐Catalyzed Highly Regioselective Arylation of Allylamines with Thiophenes and Furans

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A palladium‐catalyzed highly regioselective and stereoselective direct arylation of allylamine derivatives with a wide range of thiophenes and furans has been developed. In the presence of palladium(II) acetate [Pd(OAc)2] catalyst and appropriate oxidants, the coupling reaction proceeded with excellent group compatibility and high efficiency, leading exclusively to γ‐arylated linear (E)‐allylamines. It was found that the choice of solvent, olefin substrate and oxidant had an important influence on reaction efficiency, and the use of sterically demanding N,N‐diprotected allylamines bearing a carbamate moiety is crucial for securing high regioselectivity and stereoslectivity. This method provides a straightforward approach for the efficient synthesis of various γ‐heteroarylated, linear (E)‐allylamines.

Document Type: Research Article

DOI: http://dx.doi.org/10.1002/adsc.201200470

Affiliations: 1: Department of Chemistry, Renmin University of China, Beijing 100872, People's Republic of China, phone: (+86)-10-6251-1528, Fax: (+86)-10-6251-6444 2: Liverpool Centre for Materials and Catalysis, Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, U.K.

Publication date: November 26, 2012

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