Silver-Catalyzed Direct C–H Arylation of N-Iminopyridinium Ylides with Arylboronic Acids

Abstract

A novel direct C–H arylation of N-iminopyridinium ylides with arylboronic acids has been developed. This reaction is performed at ambient temperature using inexpensive reagents: catalytic silver nitrate in the presence of potassium persulfate co-oxidant and give pyridyl arylation derivatives in moderate to good yields.

Key words

silver - N-iminopyridinium ylides - arylboronic acids - arylation - room temperature

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• 12 N-Iminopyrinium and Boronic Acid Cross-Coupling Reaction – General Procedure A mixture of N-iminopyridinium ylide 1 (0.25 mmol), phenylboronic acid 2 (0.375 mmol), AgNO₃ (0.05 mmol), K₂S₂O₈ (0.75 mmol), TBAB (5 mol%) in CH₂Cl₂/H₂O (2 mL, 1:1) was stirring at r.t. for 8 h. Then the reaction mixture was filtered (washed with CH₂Cl₂), extracted with CH₂Cl₂ (3 × 10 mL). The combined organic phase was dried, then evaporated in vacuum. The resulting residue was purified by silica gel column chromatography to give the pure product. Compound 3fa: yellow solid. ¹H NMR (400 MHz, CDCl₃): δ = 8.67 (dd, J = 6.4, 1.0 Hz, 1 H), 8.01–7.91 (m, 3 H), 7.72 (dd, J = 8.0, 1.5 Hz, 1 H), 7.63–7.53 (m, 3 H), 7.40–7.29 (m, 3 H), 7.23 (d, J = 8.0 Hz, 2 H), 2.37 (s, 3 H). ¹³C NMR (101 MHz, CDCl₃): δ = 170.9, 153.7, 146.4, 140.9, 137.7, 137.3, 130.0, 129.5, 129.1, 128.4, 128.1, 127.8, 124.2, 21.6. ESI-HRMS: m/z [M + H]⁺: m/z calcd for C₁₉H₁₇N₂O: 289.1335; found: 289.1335. Compound 3fb: yellow solid. ¹H NMR (400 MHz, CDCl₃): δ = 8.77 (d, J = 7.2 Hz, 2 H), 8.17 (dd, J = 7.5, 2.1 Hz, 2 H), 7.81 (d, J = 7.2 Hz, 2 H), 7.60 (d, J = 8.2 Hz, 2 H), 7.44–7.34 (m, 5 H), 2.45 (s, 3 H). ¹³C NMR (101 MHz, CDCl₃): δ = 171.1, 149.6, 143.3, 141.7, 137.4, 132.3, 130.5, 129.5, 128.1, 128.0, 127.2, 123.0, 21.5. ESI-HRMS: m/z [M + H]⁺ calcd for C₁₉H₁₇N₂O: 289.1335; found: 289.1341.