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Issue 91, 2016
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Iron-catalyzed oxidative sp3 carbon–hydrogen bond functionalization of 3,4-dihydro-1,4-benzoxazin-2-ones

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Abstract

A novel and efficient iron-catalyzed sp3 carbon–hydrogen bond functionalization of benzoxazinone derivatives has been developed. For the first time, benzoxazin-2-ones were used as substrates in an oxidative dehydrogenative coupling reaction. The experiments were performed under mild reaction conditions to construct alkyl–aryl C(sp3)–C(sp2) bonds. The application of this method to the gram-scale synthesis of natural product cephalandole A has been accomplished in a 3-step sequence. A plausible one electron oxidation involved mechanism is proposed.

Graphical abstract: Iron-catalyzed oxidative sp3 carbon–hydrogen bond functionalization of 3,4-dihydro-1,4-benzoxazin-2-ones

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Publication details

The article was received on 17 Jul 2016, accepted on 08 Sep 2016 and first published on 09 Sep 2016


Article type: Communication
DOI: 10.1039/C6CC05885J
Citation: Chem. Commun., 2016,52, 13341-13344
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    Iron-catalyzed oxidative sp3 carbon–hydrogen bond functionalization of 3,4-dihydro-1,4-benzoxazin-2-ones

    C. Huo, J. Dong, Y. Su, J. Tang and F. Chen, Chem. Commun., 2016, 52, 13341
    DOI: 10.1039/C6CC05885J

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