Directing group assisted meta-hydroxylation by C-H activation

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 hydr...

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Published inChemical science (Cambridge) Vol. 7; no. 5; pp. 3147 - 3153
Main Authors Maji, Arun, Bhaskararao, Bangaru, Singha, Santanu, Sunoj, Raghavan B., Maiti, Debabrata
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2016
Subjects
Activation
Bonding
Chemistry
Chemistry, Multidisciplinary
Gain
Hydroxylation
Physical Sciences
Precursors
Quinones
Science & Technology
Solvents
Strategy
FUNCTIONALIZATION
OLEFINATION
MECHANISM
OXYGENATION
ALKYLATION
ARYLATION
ARENES
FRUSTRATED LEWIS PAIRS
BOND ACTIVATION
LIGAND
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Summary: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.
Bibliography:ObjectType-Article-1
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ISSN:2041-6520
2041-6539
DOI:10.1039/c5sc04060d