Nickel-Сatalyzed Carbon–Selenium Bond Formations under Mild Conditions

Abstract

A nickel-catalyzed C–Se cross-coupling between aryl iodides and selenols is described. The newly developed catalytic methodology offers facile access to various unsymmetrical selenium-containing motifs. The reaction features excellent functional group tolerance, wide substrate scope, good efficiency, and operates under mild reaction conditions. Notably, this protocol could be readily scaled up to gram scale without the loss of yield.

Key words

nickel catalysis - C–Se bond formation - aryl halide - cross-coupling

• References and Notes

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• 19 General Procedure A dry 5 mL vial equipped with a stirring bar was charged with an aryl iodide 1 (0.4 mmol, 2 equiv), dtbbpy (5.4 mg, 0.02 mmol, 10 mol%), Ni(COD)₂ (5.5 mg, 0.02 mmol, 10 mol%), and selenide salt 2 (if applied, 0.2 mmol, 1 equiv, without the addition of DBU) in a glovebox. Anhydrous and degassed CH₃CN (1.0 mL), phenylselenol (if applied, 21.4 μL, 0.2 mmol, 1 equiv), and DBU (59.7 μL, 0.4 mmol, 2 equiv) was added subsequently via syringe. The reaction mixture was stirred for 12 h under 40 °C. After the reaction is completed, the mixture was concentrated under vacuum and the product was purified by flash column chromatography on silica gel using hexane/EtOAc as eluent. (4-Methoxyphenyl)(phenyl)selane (3a) Yield 90% (47.7 mg). ¹H NMR (500 MHz, CDCl₃): δ = 7.56 (d, J = 8.7 Hz, 2 H), 7.39–7.36 (m, 2 H), 7.28–7.22 (m, 3 H), 6.92–6.89 (m, 2 H), 3.85 (s, 3 H). ¹³C NMR (126 MHz, CDCl₃): δ = 159.8, 136.6, 133.2, 130.9, 129.2, 126.5, 120.0, 115.2, 55.3. 4-(Cyclohexylselanyl)benzonitrile (3ac) Yield 72% (19 mg). ¹H NMR (500 MHz, CDCl₃): δ = 7.56 (dd, J = 8.3, 1.8 Hz, 2 H), 7.54–7.48 (m, 2 H), 3.46 (td, J = 10.1, 4.8 Hz, 1 H), 2.07 (dd, J = 13.4, 4.2 Hz, 2 H), 1.79 (dt, J = 14.1, 4.3 Hz, 2 H), 1.69–1.64 (m, 1 H), 1.62–1.55 (m, 2 H), 1.45–1.31 (m, 3 H). ¹³C NMR (126 MHz, CDCl₃): δ = 138.2, 132.7, 132.1, 118.9, 109.9, 43.3, 34.0, 26.7, 25.6. HRMS (ESI): m/z calcd for C₁₃H₁₅NSe [M+Na]⁺: 288.02619; found: 288.02628.