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

Christian A. Malapit, Irungu K. Luvaga, Jonathan T. Reeves*, Ivan Volchkov, Carl A. Busacca, Amy R. Howell, Chris H. Senanayake

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)4993-4997
Number of pages5
JournalJournal of Organic Chemistry
Volume82
Issue number9
DOIs
StatePublished - May 5 2017
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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