Aerobic Palladium-Catalyzed Arylation of Alkenes Using Sodium Sulfinates

Abstract

Palladium-catalyzed oxidative arylations of terminal alkenes could be performed using sodium sulfinates at 60 °C in air. The procedure gave various aryl alkenes after the desulfonylation of sodium arylsulfinates in the presence of a palladium catalyst. For instance, the reaction of styrene with sodium phenylsulfinate afforded trans-1,2-diphenylethylene in 80% yield without the formation of other stereoisomers.

Key words

oxidative arylation - alkenes - palladium catalyst - sodium arylsulfinates - Mizoroki–Heck reaction

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• 10 Typical Procedure for the Arylation of Alkenes Using Sodium Sulfinates (Table 2) To a mixture of PdCl₂ (5.3 mg, 0.03 mmol), 2,2′-bis(2-oxazoline) (4.6 mg, 0.033 mmol), PhSO₂Na (59.5 mg, 0.33 mmol), and NH₄PF₆ (14.7 mg, 0.09 mmol) in DMF (0.3 mL), H₂O (0.2 mL) and AcOH (0.1 mL) styrene (31.2 mg, 0.3 mmol) was added, and the mixture was stirred at 60 °C for 18 h in air. After the residue was dissolved in Et₂O, the solution was washed with H₂O and sat. NaCl and dried over anhyd MgSO₄. Chromatography on silica gel (hexane) gave 1,2-diphenylethene (43.0 mg, 80%).^7a Analytical Data ¹H NMR (270 MHz, CDCl₃): δ = 7.53–7.48 (m, 4 H), 7.38–7.22 (m, 6 H), 7.10 (s, 2 H) ppm. ¹³C NMR (67.5 MHz, CDCl₃): δ = 137.3, 128.7, 127.6, 126.5 ppm. Anal. Calcd for C₁₄H₁₂ (180.25): C, 93.29; H, 6.71. Found: C, 93.24; H, 6.76.
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