1,4-Addition of o-naphthoquinone methides induced by silver-catalyzed cyclization of enynones: an approach to unsymmetrical triarylmethanes and benzo[f]chromenes

Authors：Wu, Feng; Zhang, Li; Zhu, Shifa^*

Source：Organic Chemistry Frontiers, 2020, 7(21): 3387-3392.

DOI：10.1039/d0qo00825g

• FRIEDEL-CRAFTS ALKYLATION
• ORTHO-QUINONE METHIDES
• IN-SITU
• ENANTIOSELECTIVE SYNTHESIS
• EFFICIENT GENERATION
• ARYLATION
• TRIARYL
• ACCESS
• DIARYLINDOLYLMETHANES
• CYCLOADDITION

The 1,4-addition reaction of ortho-naphthoquinone methide (o-NQM) intermediates induced by silver-catalyzed ring formation with electron-rich aromatic compounds and alpha-methylene ketones has been developed. This reaction provides an efficient method to construct versatile unsymmetrical triarylmethanes and benzo[f]chromenes under mild conditions. This transient intermediate was inseparable due to reversible dimerization but could be stored by forming a boric acid adduct for further transformations.

• Institution
  南开大学; 中山大学