Molecules 2010, 15(1), 315-330; doi:10.3390/molecules15010315
Article

Palladium(II)/Cationic 2,2’-Bipyridyl System as a Highly Efficient and Reusable Catalyst for the Mizoroki-Heck Reaction in Water

Shao-Hsien Huang, Jun-Rong Chen and Fu-Yu Tsai* email
Institute of Organic and Polymeric Materials, National Taipei University of Technology, 1, Section 3, Chung-Hsiao E. Rd., Taipei 106, Taiwan
* Author to whom correspondence should be addressed.
Received: 18 December 2009; in revised form: 8 January 2009 / Accepted: 12 January 2010 / Published: 12 January 2010
(This article belongs to the Special Issue Heck Coupling)
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Abstract: A water-soluble and air-stable Pd(NH3)2Cl2/cationic 2,2’-bipyridyl system was found to be a highly-efficient and reusable catalyst for the coupling of aryl iodides and alkenes in neat water using Bu3N as a base. The reaction was conducted at 140 °C in a sealed tube in air with a catalyst loading as low as 0.0001 mol % for the coupling of activated aryl iodides with butyl and ethyl acrylates, providing the corresponding products in good to excellent yields with very high turnover numbers. In the case of styrene, Mizoroki-Heck coupling products were obtained in good to high yields by using a greater catalyst loading (1 mol %) and TBAB as a phase-transfer agent. After extraction, the residual aqueous solution could be reused several times with only a slight decrease in its activity, making the Mizoroki-Heck reaction “greener”.
Keywords: Mizoroki-Heck reaction; water-soluble catalyst; reusable; cross-coupling

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Cite This Article

MDPI and ACS Style

Huang, S.-H.; Chen, J.-R.; Tsai, F.-Y. Palladium(II)/Cationic 2,2’-Bipyridyl System as a Highly Efficient and Reusable Catalyst for the Mizoroki-Heck Reaction in Water. Molecules 2010, 15, 315-330.

AMA Style

Huang S-H, Chen J-R, Tsai F-Y. Palladium(II)/Cationic 2,2’-Bipyridyl System as a Highly Efficient and Reusable Catalyst for the Mizoroki-Heck Reaction in Water. Molecules. 2010; 15(1):315-330.

Chicago/Turabian Style

Huang, Shao-Hsien; Chen, Jun-Rong; Tsai, Fu-Yu. 2010. "Palladium(II)/Cationic 2,2’-Bipyridyl System as a Highly Efficient and Reusable Catalyst for the Mizoroki-Heck Reaction in Water." Molecules 15, no. 1: 315-330.

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