Transition-Metal-Free Acylation of Quinolines and Isoquinolines with Arylmethanols via Oxidative Cross-Dehydrogenative Coupling Reactions

Abstract

An efficient acylation of quinolines and isoquinolines is described by use of arylmethanols as the acylating agents through a C–C bond formation via an oxidative cross-dehydrogenative coupling (CDC) strategy. This C-aroylation reaction was carried out by use of K₂S₂O₈ as oxidant and methyltrioctylammonium chloride (Aliquat 336) as a transfer agent in MeCN at 80 °C under transition-metal-free conditions.

Key words

cross-dehydrogenative coupling reaction - C–C bond formation - metal-free coupling reaction - K₂S₂O₈ - Aliquat 336 - 2-aroyl quinolones - 1-aroyl isoquinolines

• References and Notes

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• 14 General Procedure for the Preparation of Compounds 3 and 5, Exemplified with 3a In a 10 mL sealable tube, benzyl alcohol (2a, 0.216 g, 2 mmol), Aliquat 336 (0.121 g, 0.3 mmol), and K₂S₂O₈ (0.675 g, 2.5 mmol) were added to a solution of isoquinoline (1a, 0.129 g, 1.0 mmol) in MeCN (3 mL). The resultant mixture was heated at 80 °C for 2 h. After completion of the reaction, as indicated by TLC, the reaction mixture was cooled to ambient temperature and treated with sat. aq NaHCO₃ (10 mL). The mixture was extracted with EtOAc (3 × 10 mL), and the combined organic layers were dried over Na₂SO₄, filtered, and the solvent was evaporated under vacuum. The residue was purified by column chromatography using n-hexane–EtOAc (8:1) as eluent to afford 3a. (Isoquinolin-1-yl)(phenyl)methanone (3a) Yield: 0.198 g (85%); white solid; mp 74–75 °C. ¹H NMR (300.1 MHz, CDCl₃): δ = 7.47 (dd, J = 7.7, 7.4 Hz, 2 H, 2 × CH), 7.60–7.63 (m, 2 H, 2 × CH), 7.75 (t, J = 7.5 Hz, 1 H, CH), 7.81 (d, J = 5.9 Hz, 1 H, CH), 7.94 (d, J = 8.6 Hz, 1 H, CH), 7.96 (d, J = 7.7 Hz, 2 H, 2 × CH), 8.20 (d, J = 8.6 Hz, 1 H, CH), 8.54 (d, J = 5.9 Hz, 1 H, CH). ¹³C NMR (75.1 MHz, CDCl₃): δ = 123.1, 125.8, 126.1, 127.3, 127.9, 128.3, 130.9, 131.2, 133.5, 136.4, 136.6, 141.7, 155.5, 194.1. (4-Chlorophenyl)(quinolin-2-yl)methanone (5c) Yield 0.187 g (70%); white solid; mp 128–129 °C. ¹H NMR (300.1 MHz, CDCl₃): δ = 7.45 (d, J = 8.5 Hz, 2 H, 2 × CH), 7.62 (t, J = 8.0 Hz, 1 H, CH), 7.75 (t, J = 7.2 Hz, 1 H, CH), 7.88 (d, J = 7.5 Hz, 1 H, CH), 8.12 (d, J = 8.7 Hz, 1 H, CH), 8.19 (d, J = 7.9 Hz, 1 H, CH), 8.24 (d, J = 8.5 Hz, 2 H, 2 × CH), 8.35 (d, J = 8.7 Hz, 1 H, CH). ¹³C NMR (75.1 MHz, CDCl₃): δ = 119.9, 127.5, 128.5, 128.9, 129.1, 130.3, 130.6, 133.3, 134.6, 137.0, 140.1, 147.2, 154.3, 193.1.