Alkane C-H Activation by Single-Site Metal Catalysis by T. Brent Gunnoe (auth.), Pedro J. Pérez (eds.)

By T. Brent Gunnoe (auth.), Pedro J. Pérez (eds.)

Over the previous decade, a lot examine attempt has been dedicated to the layout and synthesis of recent reagents and catalysts which can impression carbon-hydrogen bond activation, normally due to the prospect that C−H activation may perhaps allow the conversion of inexpensive and considerable alkanes into useful functionalized natural compounds.

Alkane C-H Activation by way of Single-Site steel Catalysis offers the present state of the art improvement within the catalytic platforms for the catalytic trans-formations of alkanes lower than homogeneous stipulations. bankruptcy 1 bargains a finished precis of the most discoveries learned thus far. bankruptcy 2 reports the so-called electrophilic activation, initiated through Shulpín within the past due 60s, and the bottom for the Catalytica process. bankruptcy three examines the catalytic borylation of alkanes, came across by means of Hartwig, while bankruptcy four offers an up to date imaginative and prescient of the alkane dehydrogenation response. bankruptcy five covers the oxygenation of C-H bonds, a box of large curiosity with bioinorganic im-plications, and eventually bankruptcy 6 provides the functionalization of alkane C-H bonds via carbene or nitrene insertion.

The historical past of C-H bond activation, and the present study defined during this booklet, spotlight the present examine and current the reader with an outlook of this box which is still explored by way of an more and more visionary and enthusiastic workforce of natural, organometallic, organic and actual chemists.

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That conclusion is consistent with most observations, but there are a couple of apparently discordant findings. Most notably, Shilov and coworkers reported that a solution used for oxidation of methane, after cooling, exhibited the NMR signal of [PtCl5(CH3)]2- [44]; if both steps 2 and 3 are significantly faster than step 1, one would not expect any significant buildup of that intermediate. (Indeed, a later examination under actual reaction conditions, using pressure-resistant NMR tubes, found no evidence of that NMR signal [45]).

Unfortunately, more detailed analysis shows that the process will almost certainly not be close to competitive with the existing route from methane via syngas to methanol [74, 75], for several reasons. First, the rates are far too low: turnover frequencies on the order of 1/s are normally the minimum required for practical processes, and that is three orders of magnitude higher than the best results found here. Next, the chemistry only works in highly concentrated (fuming) sulfuric acid, and since water is a byproduct, the medium would need to be ‘‘regenerated’’ after a short time.

73] with kind permission of Ó The American Association for the Advancement of Science (1998) be the case under more extreme conditions: a number of bis(N-ligated)Pt(II) complexes—even the simplest example, Pt(NH3)2Cl2—are moderately active for methane oxidation in concentrated sulfuric acid at 180 °C, oxidizing methane according to Eq. 14, with initial turnover rates on the order of 10-3/s. 24) persists indefinitely. Indeed, it is not only kinetically inert but thermodynamically stable: it is readily generated by adding either PtCl2 or Pt metal to a hot solution of bpym in concentrated H2SO4.

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