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Hydrocarbon Bond Activation with Platinum(II) Complexes


Chapter 1. The hydroarylation of unactivated olefins effected by Pt(II) precatalysts is found to proceed through the in situ production of protic acid followed by a Friedel-Crafts mechanism. The reaction is investigated using the hindered base 2,6-di-tert-butyl-4-methylpyridine and a variety of substrates.

Chapter 2. The catalytic cleavage of two C-C single bonds is achieved by treatment of the hydrocarbon substrate spiro[bicyclo[2.2.1]hept-2-ene-7,1'-cyclopropane] with Pt(II) catalysts such as (Me2bpy)PtPh(NTf2) (Me2bpy = 4,4'-dimethyl-2,2'-bipyridine, NTf2- = N(SO2CF3)2-). The surprising rearrangement product 1,2,4,7,7-pentahydroindene is generated in good yield. The mechanism of C-C bond activation is investigated using NMR spectroscopy, electrospray ionization mass spectrometry, and deuterium labeling, along with DFT calculations. These studies support an unusual catalytic mechanism in which an initial masked C-H bond activation initiates successive C-C bond cleavage events.

Chapter 3. A dicationic Pt complex [(tBu2bpy)Pt](NTf2)2·½ C6H6 (tBu2bpy = 4,4'-di-tert-butyl-2,2'-bipyridine) is isolated and characterized. The new complex is supported by a simple bidentate bipyridine ligand and weakly coordinating, easily displaced triflimidate counterions. The dication is competent for allylic C-H activation in aprotic, non-polar media.

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