Air-Stable Secondary Phosphine Oxides for Nickel-Catalyzed Cross-Couplings of Aryl Ethers by C–O Activation

Published as part of the 30 Years SYNLETT – Pearl Anniversary Issue

Abstract

Air- and moisture-stable secondary phosphine oxides (SPOs) enabled nickel-catalyzed Kumada–Corriu cross-couplings of various arylmethyl ethers at room temperature by challenging C–O activation.

Key words

C–O activation - arylation - cross-coupling - secondary phosphine oxide - nickel

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• 11 Representative Experimental Procedure and Characterization DataA mixture of 2-methoxynaphthalene (1a) (79 mg, 0.5 mmol), [NiCl₂(DME)] (6.0 mg, 0.025 mmol, 5.0 mol%), and L8 (8.0 mg, 0.05 mmol, 10.0 mol%) was stirred in THF (1.5 mL) for 2 min at ambient temperature under N₂. Then, p-TolMgBr (1.0 m in THF, 0.75 mL, 0.75 mmol) was added, and the resulting solution was stirred for 16 h at ambient temperature. To the reaction was added aqueous HCl (1 m, 5 mL) and then EtOAc (5 mL), and the separated aqueous phase was extracted with EtOAc (2 × 5 mL). The combined organic layers were dried with anhydrous Na₂SO₄ and concentrated in vacuo. The remaining residue was purified by column chromatography on silica gel (n-hexane) to yield 2a (98 mg, 90%) as a colorless solid. Mp 93–95 °C. IR (ATR): 3054, 3024, 1501, 1351, 893, 856, 811, 748 cm⁻¹. ¹H NMR (300 MHz, CDCl₃): δ = 8.14 (d, J = 1.4 Hz, 1 H), 8.03–7.93 (m, 3 H), 7.85 (dd, J = 8.5, 1.9 Hz, 1 H), 7.74 (d, J = 8.1 Hz, 2 H), 7.64–7.54 (m, 2 H), 7.40 (dd, J = 8.5, 0.6 Hz, 2 H), 2.53 (s, 3 H). ¹³C NMR (75 MHz, CDCl₃): δ = 138.5 (C_q), 138.3 (C_q), 137.2 (C_q), 133.8 (C_q), 132.5 (C_q), 129.6 (CH), 128.4 (CH), 128.2 (CH), 127.7 (CH), 127.3 (CH), 126.3 (CH), 125.8 (CH), 125.6 (CH), 125.5 (CH), 21.2 (CH₃). MS (EI): m/z (relative intensity) = 218 [M]⁺ (100), 217 (41), 202 (35). HRMS (EI): m/z [M]⁺ calcd for [C₁₇H₁₄]⁺: 218.1096; found: 218.1094.