Maintenance Notice (12:30 AM - 5:30 AM August 24, 2025): This website is scheduled to be unavailable due to maintenance. We appreciate your patience and understanding.
Published TCIMAIL newest issue No.198
Maximum quantity allowed is 999
Please select the quantity
TCI Practical Example: The Synthesis of α-Aminoamide Catalyzed by a Visible Light Photoredox Catalyst
We are proud to present the synthesis of an α-aminoamide from N,N-dimethylaniline and p-toluenesulfonylmethyl isocyanide by using Ir[(ppy)2(bpy)]PF6 as a visible light photoredox catalyst.
Used Chemicals
Procedure
N,N-Dimethylaniline (0.18 g, 1.5 mmol, 1.0 eq.), TosMIC (0.439 g, 2.25 mmol, 1.5 eq.), Ir[(ppy)2(bpy)]PF6(12 mg, 0.015 mmol, 1.0 mol%), ion-exchanged water (0.27 mL, 15 mmol, 10 eq.) were dissolved in acetonitrile (10 mL) at room temperature under nitrogen gas atmosphere. The mixture was placed at a distance of 2-3 cm from the Blue LED lamps. The orange solution was stirred at room temperature under visible light irradiation. After 2 days of irradiation, the solvent was removed in vacuo and the resulting residue was purified by column chromatography on silica gel (hexane:ethyl acetate = 9:1 - 1:1 - 0:1) to give compound 1 as a light brown solid (131 mg, 26% yield).
Experimenter’s Comments
- Acetonitrile was degassed with nitrogen for 1 hour before use.
- Irradiation of visible light was performed with Kessil A160WE Tuna Blue 40W x 2.
- The reaction mixture was monitored by 1H NMR and TLC (hexane:ethyl acetate = 1:1, Rf = 0.23).
Analytical Data
Compound 1
1H NMR (400 MHz, CDCl3); δ 7.72 (d, J = 8.2 Hz, 2H), 7.34-7.27 (m, 5H), 6.89 (t, J = 6.9 Hz, 1H), 6.67 (d, J = 8.7 Hz, 2H), 4.69 (d, J = 6.9 Hz, 2H), 3.75 (s, 2H), 2.99 (s, 3H), 2.45 (s, 3H).
13C NMR (101 MHz, CDCl3); δ 170.3, 148.9, 145.6, 133.6, 129.9, 129.4, 128.8, 119.2, 113.3, 59.8, 58.5, 40.0, 21.8.
Lead Reference
- Visible Light Photoredox-Catalyzed Multicomponent Reactions
Other Reference
- (review) A Retrosynthetic Approach for Photocatalysis