Abstract
Vinyl chloride (VC) reacts with the cationic Pd complexes [L2Pd(Me)(CO)][B(C6F5)4] (3a−d; L2 = Me2bipy, tBu2bipy, dppp, dmpe) and [L2Pd{C(O)Me}(CO)][B(C6F5)4] (4a−d) by 2,1-insertion of L2Pd{C(O)Me}(VC)+ intermediates to yield the O-chelated products [L2Pd{CHClCH2C(O)Me}][B(C6F5)4] (5a−d). 5a−d were characterized by NMR spectroscopy, and the molecular structures of 5a and 5b·CH2Cl2 were determined by X-ray crystallography. The VC 2,1-insertion regiochemistry is favored in part because the alternative L2Pd{CH2CHClC(O)Me}+ 1,2-insertion products would be destabilized by placement of the electron-withdrawing Cl and acyl substituents on the same carbon. In contrast to analogous nonhalogenated L2Pd{CHRCHR‘C(O)Me}+ species, 5a,c do not further react with CO, due to the stability of the chelate ring and the low migratory aptitude of the −CHClCH2C(O)Me group.
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