Copper-Catalyzed Oxidative Cross-Coupling of H-Phosphine Oxides with Alkenes in the Synthesis of Alkenylphosphine Oxides

Abstract

The first copper-catalyzed alkene oxidative cross-coupling reaction with various R₂P(O)H compounds has been reported, affording a novel and efficient method for the synthesis of valuable alkenylphosphine oxides compounds with broad substrate applicability and succinct reaction system with immoderate to good yields.

Key words

copper - alkene - phosphination - cross-coupling

• References and Notes

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• 14 Typical Procedure of Copper-Catalyzed Oxidative Cross-Coupling of H-Phosphine Oxides with Alkene to Synthesize Alkenylphosphine Oxides In a reaction tube, dicumyl peroxide (0.6 mmol, 2.0 equiv) and CuCl₂·2H₂O (0.03 mmol, 10 mol%), H(O)PPh₂ (0.30 mmol) were added and charged with Ar three times. Then, 1,1-diphenylethylene (0.90 mmol) and MeCN (3 mL) were added. The mixture was stirred at 80 °C for 12 h. After completion of the reaction, the solvent was distilled under rotary evaporation. The crude product was purified by flash chromatography on silica gel to give the desired products (PE–EtOAc, 1:1), yielding (2,2-diphenylvinyl)diphenyl-phosphine oxide as white solid (97 mg, 84%). ¹H NMR (400 MHz, CDCl₃): δ = 7.76–7.60 (m, 4 H), 7.47–7.27 (m, 11 H), 7.23 (d, J = 6.8 Hz, 2 H), 7.17–7.03 (m, 3 H), 6.79 (d, J = 18.2 Hz, 1 H). ¹³C NMR (101 MHz, CDCl₃): δ = 161.88, 161.85, 141.87, 141.71, 137.94, 137.87, 134.29 (d, J = 105.9 Hz), 130.96, 130.94, 130.80, 130.71, 130.20, 129.41, 128.52, 128.26, 128.21, 128.18, 128.09, 127.47, 120.45 (d, J = 103.7 Hz). ³¹P NMR (162 MHz, CDCl₃): δ = 18.74. ESI-MS: m/z [M + H]: 381.1407.