Divergent Reactivity of Alkyl Aryl Sulfones with Bases: Selective Functionalization of ortho??Aryl and α??Alkyl Units Enabled by a Unique Carbanion Transmetalation

L Řehová, I Císařová, U Jahn

Index: Rehova, Lucie; Cisarova, Ivana; Jahn, Ullrich European Journal of Organic Chemistry, 2014 , vol. 2014, # 7 p. 1461 - 1476

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Citation Number: 3

Abstract

Abstract The electron-accepting sulfonyl group exhibits a strong acidifying influence on neighboring α-H atoms. The Julia and related olefinations are based on this effect. Here a surprising reversal in the metalation selectivity of branched alkyl aryl sulfones is described. Such sulfones were found to initially undergo directed ortho-metalation with good regioselectivity, despite having a more acidic α-H atom. The structure of the alkyl unit ...