Synlett 2013; 24(19): 2571-2574
DOI: 10.1055/s-0033-1339846
letter
© Georg Thieme Verlag Stuttgart · New York

Aerobic Palladium-Catalyzed Arylation of Alkenes Using Sodium Sulfinates

Nobukazu Taniguchi*
Department of Chemistry, Fukushima Medical University, Fukushima 960-1295, Japan   Fax: +81(24)5471369   Email: taniguti@fmu.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 15 July 2013

Accepted after revision: 22 August 2013

Publication Date:
14 October 2013 (online)


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.

Supporting Information

 
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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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