Related Experiment Video
Updated: Jun 5, 2025

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Carbon Monoxide and Alkoxycarbonyl Radical Enabled Migration Strategy for the Carbonylative Functionalization of
Ming Hou1,2, Yuanrui Wang1, Hefei Yang1,2
1Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 116023, Dalian, Liaoning, China.
Abstract:
Herein we report a "carbonylative migration" strategy for the acylation-esterification type double functionalization of unactivated alkenes using alkyloxalkyl chlorides and CO as the reagents. The transformation is proceeded by the alkoxycarbonyl radical addition to unactivated alkenes, followed by the insertion of carbon monoxide to induce intramolecular migration of heteroaryl groups, which is different from the traditional reaction modes. The reaction conditions were mild and well tolerated with varieties of functional groups. A variety of 1,4-dicarbonyl compounds with different ester groups were produced easily which has high potential applications in biology, medicine, and other fields.
Related Concept Videos
Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation
The carbonyl center is...
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.
Hydroboration-Oxidation of Alkenes
Radical Anti-Markovnikov Addition to Alkenes: Mechanism
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy...
Alkynes to Carboxylic Acids: Oxidative Cleavage
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

