Benzyne generation from aryl triflates

PP Wickham, KH Hazen, H Guo, G Jones…

Index: Wickham, Peter P.; Hazen, Kevin H.; Guo, Hong; Jones, Garth; Reuter, Kelly Hardee; Scott, William J. Journal of Organic Chemistry, 1991 , vol. 56, # 6 p. 2045 - 2050

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Citation Number: 58

Abstract

The use of aryl triflates to form arynes as reactive intermediates is described. This allows the first general use of phenols as aryne precursors. Phenyl triflate reacts with LDA at-78" 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 ...