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Remote Para-C-H Acetoxylation of Electron-Deficient Arenes.

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One formidable challenge in sp2 C-H activation is how to achieve high para selectivity on electron-deficient arenes because such site selectivity is disfavored by the electronic bias induced by the… Click to show full abstract

One formidable challenge in sp2 C-H activation is how to achieve high para selectivity on electron-deficient arenes because such site selectivity is disfavored by the electronic bias induced by the electron-withdrawing groups. The first highly selective para-C-H acetoxylation of various benzoic acids using a nitrile-based template was realized. Removal of the template leads to para-hydroxylated benzoic acids, which are versatile intermediates for a wide range of synthetically useful transformations.

Keywords: para acetoxylation; remote para; electron deficient; deficient arenes

Journal Title: Organic letters
Year Published: 2019

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