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Stereoselective Carboperfluoroalkylation of Internal Alkynes: Mechanistic Insights

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Abstract

A Pd-catalyzed difunctionalization of internal alkynes combining boronic acids and perfluoroalkyl iodides under mild conditions is described here. Tetrasubstituted olefins containing perfluoroalkyl groups are synthesized in high yields in a regio- and stereoselective manner. Mechanistic studies have been carried out to shed light on the nature of the likely intermediates involved in these transformations.

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Acknowledgements

We thank the European Research Council (ERC Starting Grant Agreement No. 307948) for financial support.

Author information

Correspondence to Cristina Nevado.

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Li, Z., Merino, E. & Nevado, C. Stereoselective Carboperfluoroalkylation of Internal Alkynes: Mechanistic Insights. Top Catal 60, 545–553 (2017). https://doi.org/10.1007/s11244-017-0743-y

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Keywords

  • Perfluoroalkyl halides
  • Alkynes
  • Radicals
  • Boron
  • Difunctionalization