Synlett 2023; 34(12): 1381-1384
DOI: 10.1055/s-0042-1752655
cluster
Special Issue Honoring Masahiro Murakami’s Contributions to Science

Nickel-Сatalyzed Carbon–Selenium Bond Formations under Mild Conditions

Serik Zhumagazy
,
Chen Zhu
,
Huifeng Yue
,
This work was financially supported by the King Abdullah University of Science and Technology (KAUST), Saudi Arabia, Office of Sponsored Research (URF/1/4405).


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.

Supporting Information



Publikationsverlauf

Eingereicht: 22. Januar 2023

Angenommen nach Revision: 27. Februar 2023

Artikel online veröffentlicht:
31. März 2023

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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.