Directing group assisted: Meta -hydroxylation by C-H activation

Arun Maji; Bangaru Bhaskararao; Santanu Singha; Raghavan B. Sunoj; Debabrata Maiti

doi:10.1039/c5sc04060d

Directing group assisted: Meta -hydroxylation by C-H activation

Arun Maji, Bangaru Bhaskararao, Santanu Singha, Raghavan B. Sunoj, Debabrata Maiti

Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

153 Scopus citations

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.

Original language	English
Pages (from-to)	3147-3153
Number of pages	7
Journal	Chemical Science
Volume	7
Issue number	5
DOIs	https://doi.org/10.1039/c5sc04060d
State	Published - 2016

Bibliographical note

Publisher Copyright:
© The Royal Society of Chemistry 2016.

Funding

This activity is supported by SERB, India (EMR/2015/000164). Generous computing time from IIT Bombay supercomputing is acknowledged.

Funders	Funder number
Science and Engineering Research Board	EMR/2015/000164
Science and Engineering Research Board

ASJC Scopus subject areas

General Chemistry

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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.",

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AU - Singha, Santanu

AU - Sunoj, Raghavan B.

AU - Maiti, Debabrata

PY - 2016

Y1 - 2016

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AB - 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.

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Directing group assisted: Meta -hydroxylation by C-H activation

Abstract

Bibliographical note

Funding

ASJC Scopus subject areas

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