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 language | English (US) |
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Pages (from-to) | 10640-10653 |
Number of pages | 14 |
Journal | Journal of Organic Chemistry |
Volume | 86 |
Issue number | 15 |
DOIs | |
State | Published - Aug 6 2021 |
ASJC Scopus subject areas
- Organic Chemistry