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Updated: Jul 10, 2026
Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
From ynones to alkynes via nickel catalyzed decarbonylative reconstructive C-C bond coupling
Watchara Srimontree1, Manoj V Mane2, Luigi Cavallo2
1School of Chemistry, Institute of Science, Suranaree University of Technology Nakhon Ratchasima 30000 Thailand watchara.s@sut.ac.th.
None:
A distinct nickel-catalyzed intramolecular decarbonylative reconstructive C-C coupling of unstrained ynones into alkynes is described. The directing group-free protocol accommodates diverse ynones bearing (hetero)aryl, alkenyl, alkyl, and alkynyl substituents, delivering the desired products in good to excellent yields under simple conditions with low catalyst loadings and excellent functional-group tolerance. Importantly, alkyl-substituted ynones undergo efficient C(sp3)-C(sp) coupling, offering a complementary approach to alkyne synthesis beyond traditional Sonogashira-type methodologies that commonly suffer from β-hydride elimination. The synthetic utility of the method is demonstrated through late-stage modification, diynone-to-diyne formation, and preparative-scale reactions. Computational studies provide mechanistic insight into a reaction pathway that proceeds through C-C bond activation, cleavage and subsequent C-C bond formation.
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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.
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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.
02:01Alkynes to Carboxylic Acids: Oxidative Cleavage
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Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
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.
02:40Alkynes 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.