Facile One‐Pot Synthesis of 2‐Aryl‐substituted Nitriles and 2‐Aryl‐3‐keto Nitriles via Benzyne Reaction

Abstract

2‐Aryl‐substituted nitriles were prepared in good to excellent yields in a one‐pot reaction by the reaction of benzyne, generated using neutral conditions from (phenyl)[o‐(trimethylsilyl)‐phenyl]iodonium triflate, and 2‐lithionitriles. 3‐Keto nitriles substituted at the 2‐position were obtained in good yields when these reactions were trapped with acid chlorides. The mechanism of the benzyne reaction in terms of a N‐lithiobenzocyclobutanimine intermediate is discussed.

Keywords:

• benzyne
• nucleophilic addition
• Dials‐Alder reaction
• (phenyl)[o‐trimethylsilyl)‐phenyl]iodonium triflate
• 2‐aryl substituted nitriles

Acknowledgment

We thank the Robert Welch Foundation, Houston, Texas, for generous financial support of this work.