Catalytic C(sp<sup>2</sup>)–C(sp<sup>3</sup>) Bond Formation of Methoxyarenes by the Organic Superbase <i>t</i>-Bu-P4
Masanori Shigeno, Kazutoshi Hayashi, Kanako Nozawa‐Kumada, Yoshinori Kondo
Abstract
-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.
Topics & Concepts
ChemistrySuperbaseMoietyNitrileMedicinal chemistryCatalysisOrganic baseKetoneArylAmideNucleophileOrganic synthesisSalt (chemistry)Organic chemistryAlkylCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and Catalysis