A Highly Efficient and Reusable Palladium(II)/Cationic 2,2'-Bipyridyl-Catalyzed Stille Coupling in Water.
A water-soluble PdCl₂(NH₃)₂/cationic 2,2'-bipyridyl system was found to be a highly efficient catalyst for Stille coupling of aryl iodides and bromides with organostannanes. The coupling reaction was conducted at 110 °C in water, under aerobic conditions, in the presence of NaHCO₃ as a base to afford corresponding Stille coupling products in good to high yields. When aryltributylstannanes were employed, the reactions proceeded smoothly under a very low catalyst loading (as little as 0.0001 mol %). After simple extraction, the residual aqueous phase could be reused in subsequent runs, making this Stille coupling economical. In the case of tetramethylstannane, however, a greater catalyst loading (1 mol %) and the use of tetraethylammonium iodide as a phase-transfer agent were required in order to obtain satisfactory yields.
Institute of Organic and Polymeric Materials, National Taipei University of Technology, 1, Sec. 3, Chung-Hsiao E. Rd., Taipei 10608, Taiwan. willy.wu@lcygroup.com.
Wei-Yi
WY
Wu
Institute of Organic and Polymeric Materials, National Taipei University of Technology, 1, Sec. 3, Chung-Hsiao E. Rd., Taipei 10608, Taiwan. lingebubest@gmail.com.
Ling-Jun
LJ
Liu
Institute of Organic and Polymeric Materials, National Taipei University of Technology, 1, Sec. 3, Chung-Hsiao E. Rd., Taipei 10608, Taiwan. a49001103@yahoo.com.tw.
Fen-Ping
FP
Chang
Institute of Organic and Polymeric Materials, National Taipei University of Technology, 1, Sec. 3, Chung-Hsiao E. Rd., Taipei 10608, Taiwan. jacky0205333@yahoo.com.tw.
Yu-Lun
YL
Cheng
Institute of Organic and Polymeric Materials, National Taipei University of Technology, 1, Sec. 3, Chung-Hsiao E. Rd., Taipei 10608, Taiwan. fuyutsai@ntut.edu.tw.
Fu-Yu
FY
Tsai
D015082:2,2'-Dipyridyl / Q000737:chemistry*; D002384:Catalysis; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D017971:Tin Compounds / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
D009942:Organometallic Compounds; D017971:Tin Compounds; D014867:Water; C031525:stannane; D015082:2,2'-Dipyridyl; D010165:Palladium
aryl halides; organostannane; reusable; stille coupling; water-soluble catalyst