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

Autor:	Thomas L. Gianetti, Jules Moutet, Liangyong Mei, Savannah M. Stull
Rok vydání:	2021
Předmět:	Indole test Cascade Trifluoromethylation Chemistry Reagent Intramolecular force Organic Chemistry Red light Carbocation Combinatorial chemistry
Zdroj:	The Journal of Organic Chemistry. 86:10640-10653
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.1c01313
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::dd366b53176ca9635139a0aac8129068 https://doi.org/10.1021/acs.joc.1c01313 Zobrazit plný text záznamu