Reaction of aryl triflates with heteroaryllithiums via aryne intermediates

KH Reuter, WJ Scott

Index: Reuter, Kelly Hardee; Scott, William J. Journal of Organic Chemistry, 1993 , vol. 58, # 17 p. 4722 - 4726

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Citation Number: 27

Abstract

Unhindered aryl triflates react with a mixture of 1.5 equiv of LDA and 8-10 equiv of 2- lithiofuran at-78 OC to form 2-arylfurans in 5040% yield via the corresponding arynes. Regioisomeric ratios of products are similar to those observed for reactions of arynes with well-precedented nucleophiles, such as metal amides. Steric hindrance ortho to the triflate increases the cine to ipso ratio, but lowers overall yields due to enhanced nucleophilic ...