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Directing group assisted meta-hydroxylation by C-H activation.

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.

SUBMITTER: Maji A

PROVIDER: S-EPMC6005269 | biostudies-literature | 2016 May

REPOSITORIES: biostudies-literature

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Directing group assisted meta-hydroxylation by C-H activation.

Maji Arun A Bhaskararao Bangaru B Singha Santanu S Sunoj Raghavan B RB Maiti Debabrata D

Chemical science 20160121 5

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 me ...[more]

PMID: 29997806

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