Erythrosine B Catalyzed Visible‐Light Photoredox Arylation–Cyclization of N‐Alkyl‐N‐aryl‐2‐(trifluoromethyl)acrylamides to 3‐(Trifluoromethyl)indolin‐2‐one Derivatives

Abstract

3-Trifluoromethylindoline-2-one derivatives were prepared in a visible-light photocatalytic transformation of acrylamides. The arylation-cyclization sequence was initiated

Visible‐Light‐Induced 3‐Component Synthesis of Sulfonylated Oxindoles by Fixation of Sulfur Dioxide

“…NaOTs from diphenyliodonium triflate ( 1a ) . (3‐trifluoromethylphenyl)(2,4,6‐trimethoxyphenyl)iodonium triflate ( 4c ) was synthesized by adapting the literature procedure of Stuart et al Most of the N ‐acrylamides 2 were prepared from the corresponding anilines by adapting a method published by Gulder et al N ‐Methyl‐ N ‐phenyl‐2‐(trifluoromethyl)acrylamide was prepared according to a report from Novák and Tóth . Proton nuclear magnetic resonance spectra ( 1 H NMR), carbon spectra ( 13 C NMR) and fluorine spectra ( 19 F NMR) were recorded at 400 and 250 MHz ( 1 H), 126 MHz, 75 MHz ( 13 C), 471 MHz, 282 MHz ( 19 F), respectively.…”

“…[46] (3-trifluoromethylphenyl)(2,4,6-trimethoxyphenyl)iodonium triflate (4c) was synthesized by adapting the literature procedure of Stuart et al [42] Most of the N-acrylamides 2 were prepared from the corresponding anilines by adapting a method published by Gulder et al [48] N-Methyl-N-phenyl-2-(trifluoromethyl)acrylamide was prepared according to a report from Novák and Tóth. [49] Proton nuclear magnetic resonance spectra ( 1 H NMR), carbon spectra ( 13 C NMR) and fluorine spectra ( Melting points are reported uncorrected. The solvent given in brackets after the melting point is the last solvent the compound was treated with (e.g.…”

Synthesis of Cyclic Compounds via Photoinduced Radical Cyclization Cascade of C=C bonds

“…In 2013, Zou and coworkers reported a visible‐light‐mediated diarylation of N‐arylacrylamides for the synthesis of oxindoles with simultaneous construction of two C−C bond (Scheme ), wherein the aryl radical was produced via Ru 2+ * reducing the aryl diazonium salts to initiate the radical cascade cyclization. An analogous visible‐light‐induced arylation/cyclization cascade was presented by Tóth with the organic erythrosine B being applied as photocatalyst …”

Recent Advances on Metal-Free, Visible-Light- Induced Catalysis for Assembling Nitrogen- and Oxygen-Based Heterocyclic Scaffolds

“…Cyclization of N -arylacrylamides 86 have been found as a useful strategy in the synthesis of indolin-2-one compounds 88 . Novák and Tóth group developed cyclization of trifluoromethylated acrylamides under visible-light conditions catalyzed by Erythrosine B 18b (Scheme 10) [45]. The elaborated arylation/cyclization sequence is initiated by aryl radical generation from diazonium salt 87 , which undergoes addition to the double bond of 86 followed by radical cyclization.…”