Synthesis of CF3-Containing Spirocyclic Indolines via a Red-Light-Mediated Trifluoromethylation/Dearomatization Cascade

Liangyong Mei, Jules Moutet, Savannah M. Stull, Thomas L. Gianetti

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

A red-light-mediated nPr-DMQA+-catalyzed cascade intramolecular trifluoromethylation and dearomatization of indole derivatives with Umemoto's reagent has been developed. This protocol provides a facile and efficient approach for the construction of functionalized and potentially biologically important CF3-containing 3,3-spirocyclic indolines with moderate to high yields and excellent diastereoselectivities under mild conditions. The success of multiple gram-scale (1 and 10 g) experiments further highlights the robustness and practicality of this protocol and the merit of the employment of red light. Mechanistic studies support the formation of a crucial CF3 radical species and a dearomatized benzyl carbocation intermediate.

Original languageEnglish (US)
Pages (from-to)10640-10653
Number of pages14
JournalJournal of Organic Chemistry
Volume86
Issue number15
DOIs
StatePublished - Aug 6 2021

ASJC Scopus subject areas

  • Organic Chemistry

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