Development of Efficient Methods for Benzyne Generation

Abstract

2-[(Neopentyl glycolato)boryl]phenyl triflates, readily synthesized from 2-iodophenol derivatives via halogen-magnesium exchange or Miyaura borylation, were developed as new benzyne precursors. Benzynes were generated under fluoride-ion-mediated conditions and reacted immediately with various arynophiles. Herein, we describe the generation of benzynes having reactive functional groups, such as methoxycarbonyl, acetyl, bromo, and amino groups, as well as their [4+2], (3+2), and [2+2] cycloaddition reactions which produce corresponding benzo-fused compounds.