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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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Supplementary files

Article information


Submitted
26 Oct 2015
Accepted
20 Jan 2016
First published
21 Jan 2016

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2016,7, 3147-3153
Article type
Edge Article
Author version available

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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