Sulfoximines: A Reusable Directing Group for Chemo- and Regioselective ortho CH Oxidation of Arenes

Yadav, M. Ramu ; Rit, Raja K. ; Sahoo, Akhila K. (2012) Sulfoximines: A Reusable Directing Group for Chemo- and Regioselective ortho CH Oxidation of Arenes Chemistry - A European Journal, 18 (18). pp. 5541-5545. ISSN 0947-6539

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Official URL: http://doi.org/10.1002/chem.201200092

Related URL: http://dx.doi.org/10.1002/chem.201200092

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. 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.

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