By T. Brent Gunnoe (auth.), Pedro J. Pérez (eds.)
Over the earlier decade, a lot examine attempt has been dedicated to the layout and synthesis of recent reagents and catalysts that may impact carbon-hydrogen bond activation, customarily as a result of prospect that C−H activation might permit the conversion of inexpensive and ample alkanes into beneficial functionalized natural compounds.
Alkane C-H Activation via Single-Site steel Catalysis offers the present cutting-edge improvement within the catalytic structures for the catalytic trans-formations of alkanes lower than homogeneous stipulations. bankruptcy 1 deals a complete precis of the most discoveries discovered to date. bankruptcy 2 experiences the so-called electrophilic activation, initiated via Shulpín within the overdue 60s, and the bottom for the Catalytica approach. bankruptcy three examines the catalytic borylation of alkanes, came across by way of Hartwig, while bankruptcy four presents 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 offers the functionalization of alkane C-H bonds by means of carbene or nitrene insertion.
The historical past of C-H bond activation, and the present learn defined during this publication, spotlight the present study and current the reader with an outlook of this box which is still explored through an more and more visionary and enthusiastic workforce of natural, organometallic, organic and actual chemists.
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7 (reading up). The reaction shown schematically in Eq. 7 was accomplished first for S = pentafluoropyridine ; subsequently the introduction of trifluoroethanol as solvent led to an extremely versatile and richly informative model system. 8, where a stable alkyl(hydrido)Pt(IV) can be obtained via C–H activation . ½L2 PtðRÞðSÞþ þ CH4 ð2:7Þ A number of studies on the trifluoroethanol-based system have significantly increased our detailed understanding of the C–H activation process. 9 , along with the observation of extensive H/D scrambling in both the initial protonolysis of the dimethyl compound and the subsequent C–H activation, demonstrates that the rate-determining step in alkane activation3 is coordination of the alkane to give the r-complex; (reversible) C–H cleavage to give the alkyl(hydrido)Pt(IV) complex is faster.
The preference for primary site oxidation is potentially useful, since many desirable alkane oxidation targets are those derived from terminal functionalization. For example, terminal alcohols used in detergents are currently obtained via hydroformylation of olefins; alkanes would constitute a much cheaper feedstock. As noted above, most oxidations involve homolytic pathways and disfavor the stronger C–H bonds. However, Shilov chemistry exhibits fairly modest selectivity: primary H/D exchange is perhaps a factor of 2-5 or so faster than at secondary positions .
3,  on the same order as that estimated for 30 J. A. 10 Determination of relative reactivity of methane and methanol with model Pt(II) complex the actual Shilov system (see above). 7 (reading bottom to top): rate-limiting associative formation of a r complex, followed by fast oxidative cleavage of the C–H bond and deprotonation of the resulting alkyl(hydrido)Pt(IV) species. The rate-determining step is apparently not very sensitive to the nature of the coordinating species: primary and secondary C–H bonds as well as those adjacent to OH groups all react at about the same rate (after correcting for statistical factors), differing by no more than a factor of 3-5 or so.
Alkane C-H Activation by Single-Site Metal Catalysis by T. Brent Gunnoe (auth.), Pedro J. Pérez (eds.)