Palladium(II)/cationic 2,2'-bipyridyl system as a highly efficient and reusable catalyst for the Mizoroki-Heck reaction in water.
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".
Huang
Shao-Hsien
SH
Institute of Organic and Polymeric Materials, National Taipei University of Technology, 1, Section 3, Chung-Hsiao E. Rd., Taipei 106, Taiwan.
Chen
Jun-Rong
JR
Tsai
Fu-Yu
FY
D015082:2,2'-Dipyridyl / Q000737:chemistry*; D000179:Acrylates / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D002384:Catalysis; D002412:Cations / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods*; D007454:Iodides / Q000737:chemistry; D007462:Iodobenzenes / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
D000179:Acrylates; D000475:Alkenes; D002412:Cations; D007454:Iodides; D007462:Iodobenzenes; D014867:Water; D015082:2,2'-Dipyridyl; D010165:Palladium; C032490:n-butyl acrylate; C040833:ethyl acrylate; C031905:iodobenzene