Palladium-Catalyzed Cross-Coupling of Arenediazonium Salts with Organoindium or Organobismuth Reagents

Abstract

Arylindium and isolated triarylbismuth compounds generated in situ react as nucleophiles with arenediazonium salts in palladium-catalyzed cross-coupling reactions to give substituted biphenyls.

Key words

palladium catalysis - cross-coupling - arenediazonium salts - organobismuth compounds - organoindium compounds

• References and Notes

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• 51 Methyl 4-Hydroxy-3′-methoxybiphenyl-3-carboxylate (4cf); Typical Example The diazonium salt 3f (134 mg, 0.50 mmol), triarylbismuthane 7c (265 mg, 0.50 mmol, 1.0 equiv), Pd(acac)₂ (15.2 mg, 0.05 mmol, 10 mol%), and NaOAc (123 mg, 1.50 mmol, 3.0 equiv) were suspended in MeCN (0.5 mL, 1.0 M), and the mixture was stirred for 16–18 h at r.t. The mixture was then diluted with EtOAc (30 mL), washed with H₂O (30 mL), dried (MgSO₄), and concentrated in vacuo. The crude product was purified by column chromatography (silica gel, PE­–EtOAc) to give a colorless oil; yield: 66 mg (51%, 0.26 mmol). IR (ATR): 2999 (bw), 1738 (w), 1675 (m), 1204 (s), 1170 (m) cm^–1. ¹H NMR (500 MHz, CDCl₃): δ = 10.78 (s, 1 H), 8.07 (d, J = 2.2 Hz, 1 H), 7.70 (dd, J = 8.6, 2.2 Hz, 1 H), 7.35 (t, J = 7.9 Hz, 1 H), 7.13 (d, J = 7.7 Hz, 1 H), 7.09–7.03 (m, 2 H), 6.88 (dd, J = 8.2, 2.2 Hz, 1 H), 3.98 (s, 3 H), 3.87 (s, 3 H). ¹³C NMR (126 MHz, CDCl₃): δ = 170.7, 161.2, 160.2, 141.6, 134.6, 132.4, 130.0, 128.4, 119.3, 118.2, 112.7, 112.6, 112.4, 55.5, 52.5. HRMS (ESI): m/z [M + Na]⁺ calcd for C₁₅H₁₄NaO₄: 281.0784; found: 281.0787.