Related Experiment Video
Updated: Jun 16, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Photocycloaddition of enynones (4-acylbut-1-en-3-ynes) to alkenes
Inga Inhülsen1, Paul Margaretha
1Chemistry Department, University of Hamburg, D-20146 Hamburg, Germany.
Abstract:
The title compounds undergo regio- and diastereoselective [2+2]-cycloaddition at the olefinic C-C bond on irradiation (350 nm) in the presence of either methacrylonitrile or 2,3-dimethylbuta-1,3-diene, affording hitherto unknown 1-cyclobutylalk-1-yn-3-ones or 1-bicyclo[4.2.0]octylalk-1-yn-3-ones, respectively.
Related Concept Videos
Electrophilic Addition to Alkynes: Halogenation
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Cycloaddition Reactions: Overview
Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Reduction 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.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
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.

