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Updated: Jul 4, 2025
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Photoinduced selective perfluoroalkylation of terminal alkynes via electron donor-acceptor complexes
Xiaolin Shi1,2,3, Bo Yu1,2,3,4, Xin Zhou1,2,3
1CAS Key Laboratory of Bio-based Materials, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao 266101, China. yangyong@qibebt.ac.cn.
Abstract:
Herein, we report a photoinduced selective perfluoroalkylation of terminal alkynes driven by the noncovalent interaction between a thymol anion and fluoroalkyl iodides. By precisely tuning the reaction solvent, a wide range of 37 structurally diverse perfluoroalkylated alkynes and alkenes, including ibuprofen, empagliflozin, galactose, isoxepac and indomethacin, were obtained in up to 92% yields. Mechanistic studies reveal the formation of EDA complexes between the thymol anion and fluoroalkyl iodides. This strategy may provide an important complement to traditional approaches to prepare useful perfluoroalkylated alkynes and alkenes.
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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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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.
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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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