Benzyne Generation from Aryl Triflates

Article abstract of DOI:10.1021/jo00006a016

The use of aryl triflates to form arynes as reactive intermediates is decribed.This allows the first general use of phenols as aryne precursors.Phenyl triflate reacts with LDA at -78 deg C to form benzyne, which then reacts with diisopropylamine generating N,N-diisopropylaniline.Yields of diisopropylarylamines from aryne intermediates are superior to those previously reported.Regioisomeric ratios are similar to those obtained with use of other benzyne precursors.