Abstract

AbstractMild conditions are reported for the hydroxylation of aliphatic CH bonds through radical translocation, oxidation to carbocation, and nucleophilic trapping with H2O. This remote functionalization employs fac‐[Ir(ppy)3] together with Tzo sulfonate esters and sulfonamides to facilitate the site‐selective replacement of relatively inert CH bonds with the more synthetically useful COH group. The hydroxylation of a range of substrates and the methoxylation of two substrates through 1,6‐ and 1,7‐hydrogen‐atom transfer are demonstrated. In addition, a synthesis of the antidepressant fluoxetine using remote hydroxylation as a key step is presented.

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