Abstract
A merger of organocatalysis and visible light photoredox catalysis performed in flow allowed access to a wide range of functionalized N-aryl-substituted tetrahydroisoquinolines (THIQs) in a formal C-H oxidation/Mannich reaction. Strecker type functionalization and copper-catalyzed alkynylation of several N-aryl-substituted THIQs were also successfully performed in flow, giving valuable products with high efficiencies. The use of custom-made porous polymeric type microreactors proved to be crucial regarding the C-H oxidation step and overall reaction performance.
Highlights
General Remarks: All reactions were monitored by thin-layer chromatography using Merck 60 F254 precoated silica gel plates (0.25 mm thickness)
Preparative thin layer chromatography was performed using Merck 60 F254 silica gel purchased from Merck KGA
Column chromatography was carried out on silica gel (12-26, ICN Biomedicals) using petrol ether/ethyl acetate as eluents. 1H-NMR and 13C-NMR spectra were measured on a Bruker Ultrashield Advance III spectrometer (1H at 500 MHz, 13C at 125 MHz) and Varian 400 sprectrometer (1H at 400 MHz, 13C at 100 MHz) using CDCl3 as solvent with TMS as internal standard
Summary
For PDMS microreactor fabrication we used SYLGARD silicone elastomer kit 184 obtained by Dow Corning Corporation. 3.53 (m, 1H), 3.00-3.06 (m, 2H), 2.76-2.83 (m, 2H), 2.09 (s, 3H, CH3); 13C NMR (CDCl3, 125.8 MHz): δ 207.1, 156.4 (d, J = 237.6 Hz), 145.7, 138.0, 134.1, 128.8, 126.74, 126.72, 126.3, 117.1 (d, J = 7.6 Hz), 115.6 (d, J = 22.1 Hz), 55.5, 50.0, 42.6, 30.9, 26.7; 1-(2-(4-Fluorophenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)butan-2-one (2e) General procedure I was followed with 2-(4-fluorophenyl)-6,7dimethoxy-1,2,3,4-tetrahydroisoquinoline (71.8 mg, 0.25 mmol), ethyl General procedure I was followed with 6,7-dimethoxy-2-phenyl1,2,3,4-tetrahydroisoquinoline (67.3 mg, 0.25 mmol), ethyl methyl ketone (180.3 mg, 0.224 ml, 2.5 mmol), Ru(bpy)3Cl2 (1.9 mg, 0.0025 mmol), and L-proline (2.9 mg, 0.025 mmol) in MeOH
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