Related Experiment Video
Updated: Jun 12, 2026
Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Atomically Dispersed Iron-Catalyzed Aerobic Hydroxylation of Allylic and Propargylic C─H Bonds
Yijie Jiang1, Fuhua Qin1, Xu Wang2
1Key Laboratory of Material Chemistry For Energy Conversion and Storage, Ministry of Education, Hubei Key Laboratory of Material Chemistry and Service Failure, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan, China.
Abstract:
Selective functionalization of carbon-hydrogen bonds represents a central goal in modern organic synthesis, yet achieving site- and chemoselective oxidation using molecular oxygen remains a longstanding challenge. In particular, aerobic hydroxylation of allylic and propargylic C─H bonds is difficult due to overoxidation and competing side reactions. Here we report a heterogeneous catalyst featuring atomically dispersed iron sites embedded in a nitrogen-doped carbon matrix. This catalyst enables unprecedented site- and chemoselective allylic and propargylic C─H hydroxylation of alkenes and alkynes using air as the oxidant at 30°C. The method accommodates a broad range of terminal and internal substrates with excellent functional-group tolerance and enables late-stage oxidation of structurally complex molecules. Mechanistic studies demonstrate that the catalytic activity originates from highly dispersed FeNx sites. This work highlights the potential of single-atom catalysis to address fundamental challenges in sustainable C─H oxidation and expands the toolbox for selective oxidative transformations.
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
07:49Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
Published on: February 20, 2020
Related Concept Videos
02:47Alkynes 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.
02:17Reduction 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...
02:24Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
02:13Reduction 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 surface of...
02:36Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
03:08Hydroboration-Oxidation of Alkenes