4.8 Article

Programmed Sequential Additions to Halogenated Mucononitriles

Journal

ORGANIC LETTERS
Volume 22, Issue 20, Pages 8065-8069

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c03007

Keywords

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Funding

  1. UNC Chapel Hill
  2. National Science Foundation [CHE-0922858, CHE-1828183, CHE-1726291]

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Dihalomucononitriles were synthesized and their reactivity evaluated to assess their ability to function as linchpin reagents. Bis(2-chloroacrylonitrile) and bis(2-bromoacrylonitrile) were synthesized from 2,1,3-benzothiadiazole and undergo conjugate addition/elimination reactions with both nitrogen (40-95% yield) and carbon nucleophiles (72-93% yield). Secondary amines undergo monosubstitutions, while carbon nucleophiles are added twice. The sequence of addition of the nucleophiles could be controlled to give mixed addition products. The multicomponent coupling products could then be converted to natural product like motifs using intramolecular cyclization reactions.

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