Biomaterial Database

Palladium(II)/cationic 2,2'-bipyridyl system as a highly efficient and reusable catalyst for the Mizoroki-Heck reaction in water. 2010

Shao-Hsien Huang, and Jun-Rong Chen, and Fu-Yu Tsai

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

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 Bu(3)N as a base. The reaction was conducted at 140 degrees 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".

UI	MeSH Term	Description	Entries
D007454	Iodides	Inorganic binary compounds of iodine or the I- ion.	Iodide
D007462	Iodobenzenes	Any derivative of BENZENE that contains IODINE.
D010165	Palladium	A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.
D002384	Catalysis	The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction.	Catalyses
D002412	Cations	Positively charged atoms, radicals or groups of atoms which travel to the cathode or negative pole during electrolysis.	Cation
D002625	Chemistry, Organic	The study of the structure, preparation, properties, and reactions of carbon compounds. (McGraw-Hill Dictionary of Scientific and Technical Terms, 6th ed)	Organic Chemistry
D000179	Acrylates	Derivatives of acrylic acid (the structural formula CH2
D000475	Alkenes	Unsaturated hydrocarbons of the type Cn-H2n, indicated by the suffix -ene. (Grant & Hackh's Chemical Dictionary, 5th ed, p408)	Alkene,Olefin,Olefins,Pentene,Pentenes
D014867	Water	A clear, odorless, tasteless liquid that is essential for most animal and plant life and is an excellent solvent for many substances. The chemical formula is hydrogen oxide (H2O). (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	Hydrogen Oxide
D015082	2,2'-Dipyridyl	A reagent used for the determination of iron.	2,2-Bipyridine,Bipyridyl,alpha,alpha-Dipyridyl,2,2 Dipyridyl,2,2' Dipyridyl,2,2'-Bipyridine,2,2-Bipyridyl,2,2-Dipyridyl,2,2 Bipyridine,2,2 Bipyridyl,2,2' Bipyridine,Dipyridyl, 2,2,Dipyridyl, 2,2',alpha,alpha Dipyridyl