Jocelyn Pineda Lanorio - Atom transfer radical addition (ATRA) of carbon tetrachloride and chlorinated esters to various olefins catalyzed by Cp’Ru(PPh3)(PR3)Cl complexes

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  R. P. Nair, J. A. Pineda-Lanorio, B. J. Frost, Inorganica Chimica   Acta doi: 10.1016/j.ica.2011.11.008


  Cp∗Ru(PPh3)(PR3)Cl complexes, where   PR3 = PMe3, PPh3, or PTA (PTA =   1,3,5-triaza-7-phosphaadamantane), were used to catalyze the atom   transfer radical addition of chlorinated esters   (CCl3CO2Et,   CH2ClCO2Et) to styrene, and that of   CCl4 to a variety of olefins. The monoadducts were   obtained in moderate to excellent yields. Moreover, high   selectivities were obtained for the addition of CCl4  to internal olefins. The activity of   Cp∗Ru(PTA)(PPh3)Cl and Cp∗Ru(PTA)(PMe3)Cl   were comparable to that of the highly efficient ATRA catalyst,   Cp∗Ru(PPh3)2Cl. The addition of   CCl3CO2Et to styrene catalyzed by   Cp’Ru(PPh3)(PR3)Cl (Cp’ = Dp, Ind, Cp, Tp)   are also reported here. Two new compounds,   3-chloro-3-phenyl-2-(trichloromethyl)-1-phenylpropan-1-one and   1,3,3,3-tetrachloro-1,2-diphenylpropane, resulting from the   addition of CCl4 to chalcone and cis-stilbene   have been isolated and characterized by NMR spectroscopy and   X-ray crystallography.

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