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C−H Bond Activation by Dicationic Platinum(II) Complexes

Driver, Tom G. and Williams, Travis J. and Labinger, Jay A. and Bercaw, John E. (2007) C−H Bond Activation by Dicationic Platinum(II) Complexes. Organometallics, 26 (2). pp. 294-301. ISSN 0276-7333. https://resolver.caltech.edu/CaltechAUTHORS:20170725-130119305

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Abstract

Double protonolysis of diimine platinum dimethyls [(N-N)PtMe_2] (N-N ═ ArNC(Me)C(Me) ═ NAr) generates dicationic Pt(II) complexes that can activate a variety of C−H bonds, liberating 1 equiv of acid and forming organoplatinum species that are moderately stable to the resulting acidic conditions. Ethylbenzenes lead to η^3-benzyl complexes; mechanistic experiments suggest that η^3-benzyl product formation proceeds via C−H bond activation at the benzylic methylene position. In some cases π-arene complexes can be observed, but their role in the C−H activation process is not clear. Cyclohexane and 1-pentene react to give η^3-allyl complexes; allylbenzene gives a chelated phenyl-η^2-olefin structure, as determined by X-ray diffraction. No stable C−H activation products are obtained from methylbenzenes, benzene itself, or alkanes.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/0.1021/om060792rDOIArticle
http://pubs.acs.org/doi/abs/10.1021/om060792r#ChemWorx_10.1021__om060792rPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/om060792rPublisherSupporting Information
ORCID:
AuthorORCID
Labinger, Jay A.0000-0002-1942-9232
Additional Information:© 2007 American Chemical Society. Received 31 August 2006. Published online 15 December 2006. Published in print 1 January 2007. Funding for this work was provided by the bp MC2 program and the NIH in the form of NRSA fellowships to T.G.D. (Grant No. GM070272) and T.J.W. (Grant No. GM075691). We thank Tom Dunn for assistance with NMR spectrometry, Dr. Mona Shahgholi for mass spectrometry data, and Mr. Larry M. Henling for crystallographic analysis.
Funders:
Funding AgencyGrant Number
NIH Predoctoral FellowshipGM070272
NIH Predoctoral FellowshipGM075691
Issue or Number:2
Record Number:CaltechAUTHORS:20170725-130119305
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170725-130119305
Official Citation:C−H Bond Activation by Dicationic Platinum(II) Complexes Tom G. Driver, Travis J. Williams, Jay A. Labinger, and John E. Bercaw Organometallics 2007 26 (2), 294-301 DOI: 10.1021/om060792r
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:79341
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:25 Jul 2017 20:31
Last Modified:03 Oct 2019 18:19

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