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Updated: Mar 17, 2026
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Nickel-Catalyzed Hydroalkynylation of Unactivated Alkenes: Synthesis of Substituted Alkynes
Ankita Kar1, Masilamani Jeganmohan1
1Department of Chemistry, Indian Institute of Technology Madras, Chennai, Tamil Nadu 600036, India.
Abstract:
An efficient protocol for the hydrofunctionalization of unactivated long-chain olefins via a Ni(II)-catalyzed radical approach under mild conditions has been less explored. This protocol leads to the inclusion of an alkyne unit in the unactivated olefin system via the C(sp3)-C(sp) bond formation technique. This methodology has been well portrayed with various weakly and strongly coordinating amides and was also well compatible with various terminal and internal olefins. Subsequently, several control experiments have been performed, and a plausible reaction mechanism has been proposed for the detailed assessment of the reaction protocol.
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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.
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The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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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.
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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.