3 years ago

Selective Aerobic Oxidation of Methylarenes to Benzaldehydes Catalyzed by N-Hydroxyphthalimide and Cobalt(II) Acetate in Hexafluoropropan-2-ol

Selective Aerobic Oxidation of Methylarenes to Benzaldehydes Catalyzed by N-Hydroxyphthalimide and Cobalt(II) Acetate in Hexafluoropropan-2-ol
Eden Gaster, Sebastian Kozuch, Doron Pappo
Efficient and highly selective catalytic conditions for the aerobic autoxidation of methylarenes to benzaldehydes, based on N-hydroxyphthalimide (NHPI) and cobalt(II) acetate in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP), were developed. The sustainable conditions enable a multigram scale preparation of benzaldehyde derivatives in high efficiency and with excellent chemoselectivity (up to 99 % conversion and 98 % selectivity). Benzylic C−H oxidation in HFIP: The aerobic oxidation of methylarenes to benzaldehydes using N-hydroxyphthalimide (NHPI) and cobalt(II) acetate in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP) is highly selective. The mild sustainable conditions are compatible with different chemical functionalities, including alcohols and alkenes, and are suitable for oxidizing both electron-deficient and electron-efficient methylarenes.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201702511

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