Sulfoximines: A reusable directing group for chemo-and regioselective ortho C-H oxidation of arenes

Abstract

Sulfoximines direct: A new protocol for the chemo-and regioselective ortho C-H acetoxylation of arenes in N-benzoylated sulfoximines is reported. The sulfoximine directing group is easily detached from the C-H oxidation product through acid-promoted hydrolysis, isolated, and reused (see scheme). The meta-substituted phenols are synthesized following this strategy and the stereointegrity of the sulfoximine is preserved in this transformation. C(sp 3)-H acetoxylation of the methyl group is also demonstrated. © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.