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

Molecules

Shao-Hsien Huang¹  Jun-Rong Chen¹ 

[1] Institute of Organic and Polymeric Materials, National Taipei University of Technology, 1, Section 3, Chung-Hsiao E. Rd., Taipei 106, Taiwan

关键词: Mizoroki-Heck reaction;    water-soluble catalyst;    reusable;    cross-coupling;   

DOI  :  10.3390/molecules15010315

来源: mdpi

【 摘 要 】

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”.

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.