Transition metal-free direct trifluoromethylation of 2,3-Dihydropyridin-4(1H)-ones at room temperature

Yi Yun Yu, Adwait R. Ranade, Gunda I. Georg

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

A transition metal-free, regioselective C-5 trifluoromethylation of 2,3-dihydropyridin-4(1H)- ones (cyclic enaminones) with trimethyl(trifluoromethyl) silane (TMSCF3) was developed that proceeds under mild conditions at room temperature. This direct transformation was successful with both electron-rich and electron-deficient cyclic enamin- ACHTUNGTRENUNGones. This method bypasses substrate prefunctionalization and transition metal catalysis, and allows the convenient and direct access to a variety of medicinally important 3-trifluoromethylpiperidine derivatives. This chemistry also represents a rare example of a direct trifluoromethylation of an internal olefinic C-H bond. A radical mechanism is proposed for this reaction.

Original languageEnglish (US)
Pages (from-to)3510-3518
Number of pages9
JournalAdvanced Synthesis and Catalysis
Volume356
Issue number17
DOIs
StatePublished - Nov 24 2014

Bibliographical note

Publisher Copyright:
© 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords

  • C-H activation
  • Cross-coupling
  • Heterocycles
  • Radicals
  • Trifluoromethylation

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