Catalytic C(sp2)-C(sp3) bond formation of methoxyarenes by the organic superbase t-Bu-P4

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Abstract

The organic superbase catalyst t-Bu-P4 achieves nucleophilic aromatic substitution of methoxyarenes with alkanenitrile pronucleophiles. A variety of functional groups [cyano, nitro, (non)enolizable ketone, chloride, and amide moieties] are allowed on methoxyarenes. Moreover, an array of alkanenitriles with/without an aryl moiety at the nitrile α-position can be employed. The system also features no requirement of a stoichiometric base, MeOH (not salt waste) formation as a byproduct, and the production of congested quaternary carbon centers.

Original languageEnglish
Pages (from-to)9107-9113
Number of pages7
JournalOrganic letters
Volume22
Issue number22
DOIs
Publication statusPublished - 2020 Nov 20

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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