Related Experiment Video
Updated: Feb 7, 2026
05:51
Direct Detection of the Acetate-forming Activity of the Enzyme Acetate Kinase
Published on: December 19, 2011
23.7K
Directing group assisted meta-hydroxylation by C-H activation
Arun Maji1, Bangaru Bhaskararao1, Santanu Singha1
1Department of Chemistry , IIT Bombay , Powai , Mumbai-400076 , India . Email: dmaiti@chem.iitb.ac.in ;
Chemical Science
|July 13, 2018
Summary
This study introduces a novel template-assisted meta-hydroxylation reaction for C-H bond functionalization. Mechanistic insights were gained using experimental and computational methods, demonstrating synthetic utility for complex molecules.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Catalysis
Background:
- meta-Hydroxylated cores are prevalent structural motifs in numerous natural products.
- Existing methods for meta-hydroxylation often lack efficiency or broad applicability.
- Template-assisted strategies offer a promising avenue for controlled C-H functionalization.
Purpose of the Study:
- To develop the first template-assisted meta-hydroxylation reaction.
- To elucidate the reaction mechanism, including the role of hexafluoroisopropanol (HFIP).
- To demonstrate the synthetic versatility of the methodology.
Main Methods:
- Utilized a template-assisted approach for regioselective C-H hydroxylation.
- Conducted experimental studies including spectroscopic detection of reactive intermediates.
- Employed in silico (computational) methods to investigate the reaction mechanism.
- Extended the C-O bond formation to meta-acetoxylation.
Main Results:
- Successfully developed and demonstrated the first template-assisted meta-hydroxylation reaction.
- Gained mechanistic insights into the C-H activation process and the role of HFIP solvent.
- Identified and characterized reactive intermediates using spectroscopic techniques.
- Showcased the extension of the reaction to meta-acetoxylation.
- Synthesized a phase II quinone reductase activity inducer and a resveratrol precursor.
Conclusions:
- The developed template-assisted strategy provides an efficient route for meta-hydroxylation.
- Mechanistic understanding, aided by computational and experimental data, clarifies the C-H activation pathway.
- The methodology holds significant synthetic potential, as evidenced by the preparation of valuable compounds.
Related Concept Videos
01:09Directing Effect of Substituents: meta-Directing Groups
6.0K
Substituents on the benzene ring that direct an incoming electrophile to undergo substitution at the meta position are called meta directors. All meta directors either have a positive charge on the atom directly bonded to the ring or a partial positive charge. These groups function by withdrawing electrons from the ring through inductive and resonance effects. Consider the carbocation intermediates formed upon the addition of an electrophile on nitrobenzene at the...
6.0K
01:13meta-Directing Deactivators: –NO2, –CN, –CHO, –CO2R, –COR, –CO2H
6.7K
All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...
6.7K
02:26tRNA Activation
23.0K
Aminoacyl-tRNA synthetases are present in both eukaryotes and bacteria. Though eukaryotes have 20 different aminoacyl-tRNA synthetases to couple to 20 amino acids, many bacteria do not have genes for all of these aminoacyl-tRNA synthetases. Despite this, they still use all 20 amino acids to synthesize their proteins. For instance, some bacteria do not have the gene encoding the enzyme that couples glutamine with its partner tRNA. In these organisms, one enzyme adds glutamic acid to all of the...
23.0K
01:22Direct-Acting Cholinergic Agonists: Chemistry and Structure-Activity Relationship
2.2K
Cholinergic agonists or cholinomimetics mimic the action of acetylcholine to stimulate the parasympathetic nervous system. They are categorized into direct-acting and indirect-acting agents. The direct-acting cholinergic drugs induce the parasympathetic response by directly binding to the muscarinic or nicotine receptors. In comparison, the indirect-acting cholinergic drugs prevent acetylcholine hydrolysis, indirectly contributing to the extended parasympathetic response.
The direct-acting...
The direct-acting...
2.2K
01:11ortho–para-Directing Activators: –CH3, –OH, –NH2, –OCH3
7.5K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
7.5K
01:14Directing Effect of Substituents: ortho–para-Directing Groups
8.5K
Ortho–para directors are substituent groups attached to the benzene ring and direct the addition of an electrophile to the positions ortho or para to the substituent. All electron-donating groups are considered ortho–para directors. They donate electrons to the ring and make the ring more electron-rich. The ring is therefore susceptible to the addition of electrophiles. Substituents such as amino, hydroxy, or alkoxy, containing lone pairs on the atom adjacent to the ring, donate...
8.5K