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Issue 5, 2016
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Directing group assisted meta-hydroxylation by C–H activation

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Abstract

meta-Hydroxylated cores are ubiquitous in natural products. Herein, we disclose the first template assisted meta-hydroxylation reaction. Experimental and in silico studies helped us to gain valuable mechanistic insights, including the role of the hexafluoroisopropanol (HFIP) solvent, during C–H hydroxylation. The reactive intermediates, prior to the C–H activation, have been detected by spectroscopic techniques. Additionally, the C–O bond formation has been extended to meta-acetoxylation. The preparation of a phase II quinone reductase activity inducer and a resveratrol precursor illustrated the synthetic significance of the present strategy.

Graphical abstract: Directing group assisted meta-hydroxylation by C–H activation

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Publication details

The article was received on 26 Oct 2015, accepted on 20 Jan 2016 and first published on 21 Jan 2016


Article type: Edge Article
DOI: 10.1039/C5SC04060D
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Chem. Sci., 2016,7, 3147-3153
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Directing group assisted meta-hydroxylation by C–H activation

    A. Maji, B. Bhaskararao, S. Singha, R. B. Sunoj and D. Maiti, Chem. Sci., 2016, 7, 3147
    DOI: 10.1039/C5SC04060D

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