Brønsted acid-catalyzed radical CH functionalization of acetone with N-allyl anilines to give 3-(3-oxobutyl)indolines. Issue 18 (2nd May 2019)

• Record Type: Journal Article
• Authors: Wang, Xiufang; Zhao, Xiaohui; Li, Xiulan; Huo, Bojie; Dong, Ying; Liang, Deqiang; Ma, Yinhai
• Is Part Of: Tetrahedron letters. Volume 60:Issue 18(2019)
• Page Start: 1306
• Page End: 1310
• Publication Date: 2019-05-02
• Subjects: CH functionalization -- Radical cyclization -- Indolines -- Unactivated alkenes; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2019.04.017
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Brønsted acid-assisted strategy for ketonic radical generation involving K2 S2 O8 . First H + -catalyzed CH functionalization of acetone with unactivated alkenes. Difunctionalization of unactivated alkenes. 3-(3-Oxobutyl)indolines provided. exo -Selectivity and broad substrate scope. Abstract: K2 S2 O8 was unprecedentedly used instead of tert -butyl hydroperoxide (TBHP) in Brønsted acid-assisted catalytic strategy for ketonic radical generation, and the first Brønsted acid-catalyzed radical CH functionalization of acetone across unactivated alkenes is presented. In the presence of TsOH and K2 S2 O8, N -allyl anilines underwent addition/cyclization cascade with acetone to afford 3-(3-oxobutyl)indolines with exo -selectivity and broad substrate scope at a relatively low temperature.