Download e-book for kindle: 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.)

ISBN-10: 9048136970

ISBN-13: 9789048136971

ISBN-10: 9048136989

ISBN-13: 9789048136988

Over the earlier decade, a lot examine attempt has been dedicated to the layout and synthesis of recent reagents and catalysts that may impression carbon-hydrogen bond activation, customarily a result of prospect that C−H activation may well permit the conversion of inexpensive and considerable alkanes into beneficial functionalized natural compounds.

Alkane C-H Activation by way of Single-Site steel Catalysis provides the present cutting-edge improvement within the catalytic structures for the catalytic trans-formations of alkanes lower than homogeneous stipulations. bankruptcy 1 deals a finished precis of the most discoveries learned to date. bankruptcy 2 stories the so-called electrophilic activation, initiated by way of Shulpín within the past due 60s, and the bottom for the Catalytica approach. bankruptcy three examines the catalytic borylation of alkanes, came upon via 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 huge curiosity with bioinorganic im-plications, and at last 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 study defined during this ebook, spotlight the present study and current the reader with an outlook of this box which is still explored by means of an more and more visionary and enthusiastic staff of natural, organometallic, organic and actual chemists.

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12 Alternate pathways for oxidation of Zeise’s salt to an (alkyl)Pt(IV) species J. A. 13 Alternative SN2 (top) and intramolecular reductive elimination (bottom) routes for liberation of RCl from RPt(IV) H2 O [PtCl6]2H 2O -[PtCl4] 2- [Pt IVCl5(CH 2 CH 2OH)]2- -H + R Cl- IV Pt Cl RCl + PtII R Pt Cl RCl + PtII (2-hydroxyethyl)Pt(IV) species. 12); only the former would be a true analog of the redox step of the Shilov system. Kinetics established that the former path is indeed followed, and use of enriched [195PtCl6]2- led to no enrichment in the (2-hydroxyethyl)Pt(IV) product, arguing for the electron transfer route [42].

In related chemistry, Sames has found that amino acids can be selectively hydroxylated by either the original or the Cu(II)-modified Shilov system. Thus valine is converted to hydroxyvaline (obtained as the lactone) in up to 50–60 % yield and 20 turnovers. 20). 21, or perhaps subsequent to formation of a chlorinated intermediate) [64]. ), from the same group, makes use of one of the Shilov models discussed 40 J. A. 20 Proposed mechanism for selective oxidation of valine. Reprinted from Ref. 21 Competing c (top) and d (bottom) functionalization of leucine earlier: a substituted aniline containing the C–H group to be activated (the terminal end of an ethyl group) was incorporated into an imine ligand that could be coordinated to a PtMe2 group.

2 Early mechanistic proposal for C–H activation by Pt(II). Reproduced from Ref. [11] with kind permission of Ó The Royal Society of Chemistry (1971) Two additional observations gave important clues. C–H positions adjacent to quaternary centers are much less reactive, suggesting an important steric component in determining reactivity; and the distribution of CnH2n+2-xDx isotopologues was not statistical, but rather revealed a propensity for multiple exchange during each alkane-Pt encounter. 2 [11], which proceeds via rate-determining coordination of the alkane to Pt(II), followed by oxidative addition of a C–H bond to give an (alkyl)Pt(IV) hydride that can exchange with D+; multiple exchange would be explained by assuming that intermediate 3 is sufficiently stable to allow steps B and C to take place (in both directions) a number of times before alkane dissociates (the reverse of step A).

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

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