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Updated: Jul 6, 2026
Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Copper-Catalyzed Intermolecular Carbosulfonylation of Alkynes to Access Functionalized Eight-Membered
Ran Ding1,2, Jia-Nan Zhao1, Pan-Ya Cui1
1College of Chemistry and Materials Engineering, Anhui Science and Technology University, Bengbu 233000, Anhui, P. R. China.
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A copper-catalyzed tandem sulfonylation-cyclization of 3-aza-1,7-enynes with sulfonyl chlorides was developed for the efficient synthesis of sulfonylated eight-membered tetrahydroazocines in good yields and with excellent functional group compatibility. The regio- and chemoselective addition of sulfonyl radicals onto the alkynes of the tertiary enamide moiety triggers a cascade reaction followed by 8-endo cyclization, resulting in the generation of tetrahydroazocine derivatives. This transformation demonstrated a novel and efficient pathway to form eight-membered azocines, accompanied by the incorporation of a useful sulfone group.
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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.
02:24Reduction 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.
02:40Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
02:01Alkynes to Carboxylic Acids: Oxidative Cleavage
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02:38Electrophilic Addition to Alkynes: Halogenation
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