Brandon Rosen - Use of Aryl Chlorides as Electrophiles in Pd-Catalyzed Alkene Difunctionalization Reactions

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  Publication Details (including relevant citation   information):

  Rosen, B.R.; Ney, J. E.; Wolfe, J.P. J. Org. Chem.  2010, 75, 2756.


  The development of conditions that allow use of inexpensive aryl   chlorides as electrophiles in Pd-catalyzed alkene carboamination   and carboetherification reactions is described. A catalyst   composed of Pd(OAc)2 and S-Phos minimizes   N-arylation of the substrate and prevents formation of   mixtures of regioisomeric products. A number of heterocycles,   including pyrrolidines, isoxazolidines, tetrahydrofurans, and   pyrazolidines, are efficiently generated with this method.

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