Abstract
The complexes [Pt(tolpy)Cl(L)] (tolpy = 2-(4-tolyl)pyridyl; L = dmso, dms, py, PPh3, CO) are precursors for the catalytic cleavage of C–C bonds and extrusion of CO from a series of unactivated keto...
Highlights
Dong and co-workers have developed an elegant catalytic strategy for Cα−CCO bond activation in which the carbonyl is activated by catalytic amounts of amine or carbene and the thermodynamic driving force is provided by concomitant formation of new C−C bonds.[26]
Given the known photochemical instability of cyclohexanone and cyclopentanone in the gas phase,[33] and reports of photochemical C−C bond activations,[34] control experiments established that activation of cyclohexanone mediated by 1 proceeded in the absence of natural light to give the same products
Irradiation of a room-temperature solution of 1 in cyclohexanone at room temperature led to no observable reaction, confirming that the decarbonylation is thermal in nature
Summary
Examples of Metal-Mediated C−C Activation of Ketonic Substrates with Strained[10] or Tethered[4,16,26] Substrates made that heating [Pt(tolpy)(Cl)(S-dmso)] (1; tolpy = 2-(4tolyl)pyridyl) in air with cyclohexanone afforded the known[32] complex [Pt(tolpy)(Cl)(CO)] (2; Scheme 2), characterized by νCO 2098 cm−1, δ(195Pt) −3947 ppm and by single-crystal X-ray methods (see the Supporting Information for details). GC and GC-MS analysis of the headspace gas after reaction of cyclohexanone with 1 confirmed the formation of butane and methane, with trace amounts of other small hydrocarbons (see Scheme 2), as detailed in the Supporting Information.
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