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CsF-Mediated in Situ Desilylation of TMS-Alkynes for Sonogashira Reaction

Joseph S Capani1, John E Cochran1, Jianglin Colin Liang1

  • 1Vertex Pharmaceuticals Incorporated , 50 Northern Avenue , Boston , Massachusetts 02210 , United States.

The Journal of Organic Chemistry
|June 14, 2019
PubMed

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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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The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
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