Copper-Catalyzed Aerobic Oxidation and Oxygenation of Anilines and Acetaldehydes with Dioxygen for the Concise Synthesis of 2-Aroylquinolines

Abstract

A concise and efficient aerobic oxidation and oxygenation approach for the construction of 2-aroylquinolines has been developed through copper-catalyzed annulation of anilines, acetaldehydes, and dioxygen. 2,2,6,6-Tetramethylpiperidine-1-oxyl was employed to direct the selectivity toward the desired 2-aroyl products. Molecular oxygen was used in this transformation as an environmentally benign source of oxygen.

Key words

2-aroylquinolines - oxygenation - anilines - acetaldehydes - copper catalysis - aerobic oxidation - annulation

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• 15 Phenyl(3-phenylquinolin-2-yl)methanone (9a); Typical Procedure To a reaction tube charged with CuNO₃·3 H₂O (12.1 mg, 0.05 mmol, 20 mol%) and TEMPO (78.1 mg, 0.5 mmol, 2 equiv) under O₂ (1 atm) was added a solution of aniline (2a, 0.25 mmol, 1 equiv), phenylacetaldehyde (3a, 1 mmol, 4 equiv), and H₂O (135 μL, 7.5 mmol, 30 equiv) in DMF (3 mL). The mixture was stirred at 100 °C for 12 h then cooled to r.t. The mixture was diluted with EtOAc, washed with sat. aq NaHCO₃, water, and brine, dried (Na₂SO₄), and concentrated in vacuo to give dark residue that was purified by flash chromatography [silica gel, PE–EtOAc (50:1 to 30:1)] to give an off-white oil; yield: 55 mg (71%). ¹H NMR (400 MHz, CDCl₃): δ = 8.28 (s, 1 H), 8.19 (d, J = 8.4 Hz, 1 H), 7.86–7.94 (m, 3 H), 7.76–7.80 (m, 1 H), 7.64–7.68 (m, 1 H), 7.52–7.56 (m, 1 H), 7.38–7.41 (m, 4 H), 7.30–7.33 (m, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 195.1, 156.3, 146.1, 137.7, 137.2, 136.2, 134.1, 133.5, 130.5, 130.1, 129.7, 129.0, 128.6, 128.4, 128.1, 128.0, 127.9, 127.8. HRMS (ESI): m/z [M + H]⁺ calcd for C₂₂H₁₆NO: 310.1232; found: 310.1226.