Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

1,4-Dicarbofunctionalization of 4-Fluoroaryl Grignard and Lithium Reagents with Disubstituted Malononitriles

1,4-Dicarbofunctionalization of 4-Fluoroaryl Grignard and Lithium Reagents with Disubstituted Malononitriles
Jonathan T. Reeves, Ivan Volchkov, Irungu K. Luvaga, Christian A. Malapit, Carl A. Busacca, Amy R. Howell, Chris H. Senanayake
An efficient one-pot 1,4-dicarbofunctionalization of 4-fluoroaryl Grignard or lithium reagents with 2,2-disubstituted malononitriles is described. The reaction proceeds by sequential transnitrilation and SNAr reactions. Commercial Grignard solutions, Grignard reagents prepared in situ by halogen/magnesium exchange with i-PrMgCl, or aryllithium reagents prepared in situ by bromine/lithium exchange with n-BuLi are compatible with the reaction conditions. Moreover, 2,2-disubstituted malononitriles of diverse structures are accommodated. The reaction provides a unique approach to 1,4-dicarbofunctionalization of activated arenes in a tandem, one-pot transformation.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00567

DOI: 10.1021/acs.joc.7b00567

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