Palladium/Sensory Component-Catalyzed Homocoupling Reactions of Aryl Halides

Dedicated to Ms. Gailian Xiao

Abstract

A novel and efficient catalyst system was developed for homocoupling reactions of aryl halides. The catalyst system consists of Pd(OAc)₂ and the peppery sensory component of tobacco leaves. This is the first time that a sensory component has been used in an organic reaction. Experiments using the catalyst system showed that the reactions proceeded smoothly under air in the absence of both an additional ligand and a reductant. Furthermore, the catalyst system can be applied to the coupling reactions of hetaryl iodides. Many functional groups (including a hydroxy group) are tolerated.

Key words

palladium catalyst - sensory component - homocoupling - aryl halides - biaryls

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• 27 Bi(het)aryls 2a–y; General Procedure The appropriate (het)aryl halide 1 (0.5 mmol) was added to a mixture of Pd(OAc)₂ (0.05 mmol, 10 mol%), sensory component (8 mg), and K₂CO₃ (1.0 mmol, 2 equiv) in DMF (10 mL), and the mixture was stirred and heated in an oil bath at 100 °C for 24 h. The mixture was then extracted with EtOAc (3 × 20 mL). The combined organic phases were dried (MgSO₄), filtered, concentrated under reduced pressure, and purified by column chromatography (silica gel). 3,3′,4,4′,5,5′-Hexamethoxy-1,1′-biphenyl (2g) Prepared by the general procedure from 5-iodo-1,2,3-trimethoxybenzene (1g) and purified by column chromatography [silica gel, EtOAc–PE (1:3)] as a light-yellow solid; yield: 48 mg (58%); mp 127.2 °C. ¹H NMR (400 MHz, CDCl₃): δ = 6.72 (s, 4 H), 3.93 (s, 12 H), 3.89 (s, 6 H). ¹³C NMR (100 MHz, CDCl₃): δ = 153.4, 137.7, 137.6, 104.6, 61.0, 56.3. HRMS: m/z [M + H]⁺ calcd for C₁₈H₂₃O₆: 335.1494; found: 335.1491.