Synlett 2014; 25(19): 2727-2732
DOI: 10.1055/s-0034-1379545
cluster
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Oxidative Cross-Coupling of H-Phosphine Oxides with Alkenes in the Synthesis of Alkenylphosphine Oxides

Liu-Liang Mao
a  State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China   Fax: +86(931)8912859   Email: yangshd@lzu.edu.cn
,
An-Xi Zhou
a  State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China   Fax: +86(931)8912859   Email: yangshd@lzu.edu.cn
,
Na Liu
a  State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China   Fax: +86(931)8912859   Email: yangshd@lzu.edu.cn
,
Shang-Dong Yang*
a  State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China   Fax: +86(931)8912859   Email: yangshd@lzu.edu.cn
b  State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, P. R. of China
› Author Affiliations
Further Information

Publication History

Received: 11 September 2014

Accepted after revision: 30 October 2014

Publication Date:
06 November 2014 (online)


Abstract

The first copper-catalyzed alkene oxidative cross-coupling reaction with various R2P(O)H compounds has been reported, affording a novel and efficient method for the synthesis of valuable alkenylphosphine oxides compounds with broad substrate applicability and succinct reaction system with immoderate to good yields.

Supporting Information

 
  • References and Notes

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  • 14 Typical Procedure of Copper-Catalyzed Oxidative Cross-Coupling of H-Phosphine Oxides with Alkene to Synthesize Alkenylphosphine Oxides In a reaction tube, dicumyl peroxide (0.6 mmol, 2.0 equiv) and CuCl2·2H2O (0.03 mmol, 10 mol%), H(O)PPh2 (0.30 mmol) were added and charged with Ar three times. Then, 1,1-diphenylethylene (0.90 mmol) and MeCN (3 mL) were added. The mixture was stirred at 80 °C for 12 h. After completion of the reaction, the solvent was distilled under rotary evaporation. The crude product was purified by flash chromatography on silica gel to give the desired products (PE–EtOAc, 1:1), yielding (2,2-diphenylvinyl)diphenyl-phosphine oxide as white solid (97 mg, 84%). 1H NMR (400 MHz, CDCl3): δ = 7.76–7.60 (m, 4 H), 7.47–7.27 (m, 11 H), 7.23 (d, J = 6.8 Hz, 2 H), 7.17–7.03 (m, 3 H), 6.79 (d, J = 18.2 Hz, 1 H). 13C NMR (101 MHz, CDCl3): δ = 161.88, 161.85, 141.87, 141.71, 137.94, 137.87, 134.29 (d, J = 105.9 Hz), 130.96, 130.94, 130.80, 130.71, 130.20, 129.41, 128.52, 128.26, 128.21, 128.18, 128.09, 127.47, 120.45 (d, J = 103.7 Hz). 31P NMR (162 MHz, CDCl3): δ = 18.74. ESI-MS: m/z [M + H]: 381.1407.