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Skeletal Editing of Alkenes and Alkynes via Single-Carbon-Atom Insertion
Wei Jiang1, Yaxin Fan2, Fukuan Zhang2
1School of Chemistry and Molecular Engineering, College of Materials Science and Engineering, Nanjing Tech University, Nanjing, 211816, China.
Abstract:
Skeletal editing has emerged as a pivotal complement to retrosynthetic analysis strategies. This approach enables simple bulk chemical feedstocks to achieve precise atomic-level modifications-such as insertion, deletion, or swapping-facilitating the rapid assembly of complex, high value-added functional organic molecules. Currently, single-carbon-atom insertion reactions predominantly emphasize the functionalization of (hetero)aromatic systems, leaving the site-specific editing of unsaturated C─C bond frameworks such as alkenes and alkynes, comparatively underexplored. This review provides detailed analysis and summary of recent progress in the skeletal editing of functional alkenes and alkynes derivatives via single-carbon-atom insertion, and outlining the future potential directions of this technology.
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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.
02:47Alkynes 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.
02:38Electrophilic Addition to Alkynes: Halogenation
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