Selective monoarylation of benzenediols via dianion intermediates

C Xie, KA Sullivan, ME Laurila, DN Mitchell…

Index: Xie, Chaoyu; Sullivan, Kevin A.; Laurila, Michael E.; Mitchell, David N.; Pu, Y. John Synthetic Communications, 2008 , vol. 38, # 1 p. 21 - 32

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Abstract

Abstract Application of the SNAr reaction on benzenediols with arylfluorides revealed an enhancement in monosubstitution selectivity over bis substitution when excess base was used. This trend was studied using symmetrical and nonsymmetrical benzenediols with various levels of steric hindrance. The effect of various bases was examined. A 100% monoselectivity was achieved in the presence of 2.5 equiv. of Cs2CO3. The methodology ...

~84%

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