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• W2903798735 abstract "Despite significant progress in the development of site-selective aliphatic C–H oxidations over the past decade, the ability to oxidize strong methylene C–H bonds in the presence of more oxidatively labile aromatic functionalities remains a major unsolved problem. Such chemoselective reactivity is highly desirable for enabling late-stage oxidative derivatizations of pharmaceuticals and medicinally important natural products that often contain such functionality. Here, we report a simple manganese small-molecule catalyst Mn(CF3–PDP) system that achieves such chemoselectivity via an unexpected synergy of catalyst design and acid additive. Preparative remote methylene oxidation is obtained in 50 aromatic compounds housing medicinally relevant halogen, oxygen, heterocyclic and biaryl moieties. Late-stage methylene oxidation is demonstrated on four drug scaffolds, including the ethinylestradiol scaffold where other non-directed C–H oxidants that tolerate aromatic groups effect oxidation at only activated tertiary benzylic sites. Rapid generation of a known metabolite (piragliatin) from an advanced intermediate is demonstrated. A small-molecule manganese-based catalyst has been developed for the selective oxidation of strong methylene C–H bonds in the presence of more oxidatively labile aromatic functionality. This reaction enables the late-stage oxidative derivatization of medicinally relevant compound scaffolds and may also prove useful for diversifying aromatic drugs and natural products, as well as helping to quickly identify their metabolites." @default.
• W2903798735 created "2018-12-22" @default.
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• W2903798735 date "2018-12-17" @default.
• W2903798735 modified "2023-10-16" @default.
• W2903798735 title "Chemoselective methylene oxidation in aromatic molecules" @default.
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• W2903798735 doi "https://doi.org/10.1038/s41557-018-0175-8" @default.
• W2903798735 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/6386604" @default.
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