4.7 Article

Atom-Efficient, Palladium-Catalyzed Stille Coupling Reactions of Tetraphenylstannane with Aryl Iodides or Aryl Bromides in Polyethylene Glycol 400 (PEG-400)

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 351, Issue 9, Pages 1378-1382

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200800754

Keywords

aryl bromides; aryl iodides; atom efficiency; polyethylene glycol 400 (PEG-400); Stille coupling; tetraphenylstannane

Funding

  1. Natural Science Foundation of China [20272047, 20572086]
  2. Gansu Natural Science Foundation of China [0308RJZA-100]
  3. Key Laboratory of Eco-Environment-Related Polymer Material (Northwest Normal University), Ministry of the Education of China

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The Stille coupling of tetraphenylstannane with aryl iodides or aryl bromides using the bis(triphenylphosphine)palladium dichloride/sodium acetate/polyethylene glycol 400 [PdCl2(PPh3)(2)/NaOAc/PEG-400] catalytic system at 100 degrees C has been developed. The reactions were carried out in an atom-efficient way, as 4 equivalents of aryl iodides or aryl bromides coupled effectively with 1 equivalent of tetraphenylstannane to furnish 4 equivalents of the corresponding functionalized biaryls in high yields.

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