Related Experiment Video
Updated: Jul 26, 2025

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
Published on: November 29, 2018
Aerobic Oxidative N-Heterocyclic Carbene Catalysis
Simon Stenkvist1, Sara Bacaicoa1, Ellymay Goossens1
1Chemistry and Molecular Biology, University of Gothenburg, Kemivägen 10, 41296, Gothenburg, Sweden.
Aerobic oxidative catalysis using N-heterocyclic carbenes (NHCs) offers a sustainable alternative to traditional methods. This review explores NHC-catalyzed reactions employing oxygen as a green oxidant, addressing challenges and advancements.
Area of Science:
- Organic chemistry
- Catalysis
- Green chemistry
Background:
- Oxidative N-heterocyclic carbene (NHC) catalysis is valuable for synthesizing functionalized products from simple precursors.
- Traditional methods often rely on stoichiometric oxidants, generating significant waste.
- Developing catalytic systems using oxygen as a terminal oxidant is crucial for sustainability.
Purpose of the Study:
- To review the advancements in aerobic oxidative carbene catalysis.
- To discuss strategies for activating molecular oxygen in NHC catalysis.
- To highlight selectivity challenges and solutions in oxygen-based NHC reactions.
Main Methods:
- Literature review of NHC-catalyzed aerobic oxidation reactions.
- Analysis of oxygen activation strategies in catalytic cycles.
- Examination of factors influencing selectivity under aerobic conditions.
Main Results:
- NHC catalysis with oxygen offers a greener synthetic route, producing water as the main byproduct.
- Various strategies have been developed to overcome the challenges of using unreactive molecular oxygen.
- Understanding and controlling selectivity remains a key focus in aerobic oxidative carbene catalysis.
Conclusions:
- Aerobic oxidative carbene catalysis presents a promising, environmentally friendly approach to organic synthesis.
- Continued research into oxygen activation and selectivity is vital for broader application.
- This catalytic approach minimizes waste and utilizes a cost-effective oxidant.
More Related Videos
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
Published on: June 20, 2014
07:06A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Related Concept Videos
Catalysis
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Phase I Reactions: Oxidation of Carbon-Heteroatom and Miscellaneous Systems
In carbon-nitrogen systems, aliphatic and aromatic amines can undergo oxidative reactions. Secondary and tertiary amines, like those found in tricyclic antidepressants, can undergo N-dealkylation, a process that involves the oxidation of the alkyl group. In addition, oxidative...
Oxidative Cleavage of Alkenes: Ozonolysis
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
Reduction of Alkenes: Catalytic Hydrogenation
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...