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Related Concept Videos

Reactions at the Benzylic Position: Oxidation and Reduction00:59

Reactions at the Benzylic Position: Oxidation and Reduction

4.9K
The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.
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Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

5.7K
Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
5.7K
Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

3.5K
Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
3.5K
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

2.6K
Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
2.6K
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

11.1K
In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
11.1K
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

12.6K
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
12.6K

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Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of &#945;,&#946;-Unsaturated Compounds and Alkynes
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Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

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Selective Toluene Electrooxidation to Benzyl Alcohol.

Madeleine K Wilsey1, Nathalia Cajiao2,3, Aleksa Radovic2

  • 1Materials Science Program, University of Rochester, Rochester, New York 14627, United States.

Journal of the American Chemical Society
|September 24, 2025
PubMed
Summary

This study introduces a new electrocatalytic method for oxidizing toluene to benzyl alcohol using water as an oxygen source. The process utilizes novel catalysts and wet organic solvents to achieve high selectivity and yield, offering a sustainable synthesis route.

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Area of Science:

  • Electrochemistry
  • Catalysis
  • Organic Synthesis

Background:

  • Hydrocarbon oxidation is crucial for chemical synthesis but often suffers from low selectivity and overoxidation.
  • Water is a sustainable and environmentally friendly oxygen source for oxidation reactions.
  • Developing efficient electrocatalytic systems for selective hydrocarbon functionalization remains a challenge.

Purpose of the Study:

  • To develop a novel electrocatalytic approach for selective toluene oxidation using water as the oxygen source.
  • To investigate the role of wet organic solvents (DMF and DMSO) in mediating the oxidation reaction.
  • To elucidate the reaction mechanism and identify factors controlling selectivity and conversion.

Main Methods:

  • Electrocatalytic oxidation of water and toluene in wet N,N-dimethylformamide (DMF) and dimethyl sulfoxide (DMSO) electrolytes.
  • Utilization of laser-synthesized [NiFe]-(OH)2 nanosheets supported on carbon fiber paper as anode catalysts.
  • Combined experimental studies and computational modeling to understand the reaction mechanism.

Main Results:

  • High selectivity (100%) for benzyl alcohol production from toluene oxidation in wet DMF electrolyte with an 87% conversion yield.
  • Identification of hydroxyl (·OH) radical formation as the key intermediate, favored by solvent-mediated hydrogen bonding.
  • Demonstrated prevention of overoxidation to benzoic acid due to stabilization of radical intermediates.

Conclusions:

  • A novel electrocatalytic pathway for selective hydrocarbon oxidation has been established, coupling water oxidation with toluene oxidation.
  • Wet organic solvents play a critical role in stabilizing reactive intermediates and controlling reaction selectivity via hydrogen bonding.
  • The findings provide fundamental design principles for sustainable and selective oxidation reactions with broad synthetic implications.