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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 20
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Original Articles

Ruthenium-Catalyzed Coupling Reaction of Benzylic Halides

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Pages 3583-3588 | Received 17 Mar 2003, Published online: 15 Aug 2006

References

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  • Tris-triphenylphosphine ruthenium(II) dichloride RuCl2(PPh3)3was prepared according to the literature procedure.[13]The solvents were used without further purification. Melting point was determined on a Micro capillary melting point apparatus and uncorrected.1H NMR was recorded on Varian 500 MHz spectrometer. All reactions were run in autoclave under hydrogen atmosphere (15 kg/cm2). Alpha chlorodiohenylethane (2a, 1.0 g, 5.0 mmol), RuCl2(PPh3)3(0.049 g, 0.05 mmol), and benzene (20 mL) were added to autoclave (100 mL), under 15 kg/cm2hydrogen pressure at 90°C stirring for 24 h. After removal of benzene, the cruel product was purified by recrystallization with chloroform to give 1,1,2,2-tetraphenylethane 3a as a colorless needle crystal 0.78 g (95%). 3a M.p.: 212°C.1H NMR (CDCl3, 500 MHz) δ: 4.77 (2H, s), 6.99–7.17 (20H, m).13C NMR (CDCl3, 500 MHz) δ: 57.05, 126.55, 128.84, 129.22, 144.17. IR (KBr) cm−1: 3420, 3025, 3014, 1494, 1449, 1072, 746, 698, 608. 3b M.p.: 178°C.1H NMR (CDCl3, 500 MHz) δ: 2.17 (6H, d,J = 8.6 Hz), 4.72 (2H, s), 6.89–7.11 (18H, m).13C NMR (CDCl3, 500 MHz) δ: 21.65, 56.58, 126.38, 128.82, 129.00, 129.15, 129.55, 135.83, 141.30, 144.62. IR (KBr) cm−1: 3430, 3019, 2913, 1513, 1492, 1108, 1070, 788, 723, 694. 3c M.p.: 221–222°C.1H NMR (CDCl3, 500 MHz) δ: 4.70 (2H, dd,J = 20.3 Hz,J = 6.3 Hz), 7.04–7.28 (18H, m).13C NMR (CDCl3, 500 Hz) δ: 57.04, 126.55, 126.68, 128.85, 128.98, 129.05, 129.13, 129.22, 130.92, 131.96, 142.92, 144.17. IR (KBr) cm−1: 3060, 3023, 2890, 1489, 1448, 1072, 1008, 744, 696
  • Hallam , P.S. , Stephenson , T.A. and Wilkinson , G. 1972 . Inorg. Synth. , 12 : 238

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