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Updated: Jan 15, 2026
Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Base-Promoted Nucleophile Addition to Arynes Generated from Triaryloxonium Salts
Sheng Fang1, Wang-Liang Chen1, Yuan-Jie Meng2
1School of Pharmacy, Guangdong Pharmaceutical University, Guangzhou 510006, P. R. China.
None:
In this study, a facile method for the synthesis of aryl-substituted esters, amides, α-aryl sulfoxonium ylides, thioethers, aryl-quinolinones/isoquinolinones via nucleophilic addition reaction of oxonium aryne precursors with corresponding carboxylic acids, isocyanides, sulfoxonium ylides, mercaptans, trifluoromethyl silver, and halogenated quinolines/isoquinolines has been developed. This protocol featured mild reaction conditions, a high yield, and a good tolerance of functional groups. In addition, scale-up synthesis and related applications were also accomplished.
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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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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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