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Updated: May 27, 2025
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Selective hydrophosphorylation of alkynes for the synthesis of (E)-vinylphosphonates
Babak Kaboudin1, Hesam Esfandiari1, Nematollah Arshadi2
1Department of Chemistry, Institute for Advanced Studies in Basic Sciences Gava Zang Zanjan Iran kaboudin@iasbs.ac.ir kaboudin@gmail.com +98 24 33153232 +98 24 33153220.
Abstract:
Hydrophosphorylation of alkynes with dialkylphosphites in the various copper catalysts was investigated. The reactions provided the regio- and stereoselective E-vinylphosphonates under commercially available copper chloride catalyst in the presence of ethylene diamine as an efficient ligand. The impact of solvents, temperature, and diamine ligands are included in this report. In addition, the DFT calculations provided insight into the regio- and stereoselectivity of the reaction. It is suggested that the reaction proceeded via an in situ generated Cu(AN)4 + complex. The reaction of phenylacetylene with diethyl phosphite in the presence of EDA and the (CH3CN)4CuBF4 complex as a catalyst also gave the corresponding E-vinylphosphonates in good yield.
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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.
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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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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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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.
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