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Catalytic α-Monoallylation of Aryl Acetonitriles

Tapan Maji and Jon A. Tunge*

*Department of Chemistry, The University of Kansas, 2010 Malott Hall, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, United States, Email: tungeku.edu

T. Maji, J. A. Tung, Org. Lett., 2014, 16, 5072-5075.

DOI: 10.1021/ol5024294 (free Supporting Information)


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Abstract

α-Cyano aldehydes undergo selective transition-metal-catalyzed allylation to provide α-allylated nitriles. The transformation leads to linear allylated nitriles with palladium catalysts whereas an iridium catalyst provides branched substitution products. TBD-catalyzed retro-Claisen cleavage is leveraged to attain selective monoallylation.


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Key Words

nitriles, allylation


ID: J54-Y2014