Peroxide-Promoted Regioselective Arylation of 2-Phenylpyridines and Related Substrates with Aryl Iodides

Abstract

The direct arylation of aryl iodides with 2-phenylpyr­idines and related substrates was carried out smoothly in the presence of 5 mol% RuCl₃ using benzoyl peroxide as a promoter to generate biarylated products in high yields. The method is simple, efficient, and regioselective, and employs only commercially available reagents.

Key words

C-H activation - arylation - ruthenium homogeneous catalysis

References and Notes

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General Procedure
Starting materials and solvents were purchased from common commercial sources and were used without additional purification. Column chromatography was carried out on SiO₂ (300-400 mesh). ¹H NMR spectra were recorded at 400 MHz, ¹³C NMR spectra were recorded at 100 MHz, using TMS as internal standard. Mass spectrometry data of the product of direct arylation reaction were collected on an HRMS-EI instrument.

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General Procedure for Direct Arylation Reaction A mixture of K₂CO₃ (2 mmol), RuCl₃ (11 mg, 5 mol%),
2-phenylpyridines (1 mmol), aryl iodines (2.4 mmol), peroxybenzoic (1 mmol), and NMP (5 mL) was stirred at 150 °C for 12 h. Afterwards, the reaction solution was cooled to r.t. and filtered through a filter paper. Brine (20 mL) was added to the filtrate and the mixture was extracted three times with EtOAc (3 × 15 mL). After washing with H₂O (3 × 20 mL) and brine (20 mL), the combined organic phase was evaporated under reduced pressure. The residue was purified on a SiO₂ column to afford the desired product.