Activation and Functionalization of C-H Bonds

ACS Symposium Series Volume 885

Karen I. Goldberg and Alan S. Goldman, Editors

ACS referencing: To reference a chapter (please note that chapter title should be included):

Author, A. A.; Author, B. B. Chapter Title. In Activation and Functionalization of C-H Bonds;

Goldberg, K. I.; Goldman, A. S., Eds.; ACS Symposium Series 885; American Chemical Society:

Washington, DC, 2004, pp xx-yy.

To reference entire book:

Goldberg, K. I.; Goldman, A. S., Eds. Activation and Functionalization of C-H Bonds;

ACS Symposium Series 885; American Chemical Society: Washington, DC, 2004.

Preface ........................................................................................................................ xi

1. Organometallic C–H Bond Activation: An Introduction ....................................... 1 pdf

Alan S. Goldman and Karen I. Goldberg

Oxidative Addition Reactions

2. Carbon–Hydrogen Bond Activation by Iridium and Rhodium Complexes:

Catalytic Hydrogen/Deuterium Exchange and Carbon-Carbon

Bond-Forming Reactions ..................................................................................... 46 pdf

Steven R. Klei, Kian L. Tan, Jeffrey T. Golden, Cathleen M. Yung, Reema K. Thalji,

Kateri A. Ahrendt, Jonathan A. Ellman, T. Don Tilley, and Robert G. Bergman

3. Alkane Complexes as Intermediates in C–H Bond Activation Reactions ............ 56 pdf

William D. Jones, Andrew J. Vetter, Douglas D. Wick, and Todd O. Northcutt

4. C–C versus C–H Bond Oxidative Addition in PCX (X=P,N,O) Ligand Systems:

Facility, Mechanism and Control ....................................................................... 70 pdf

Boris Rybtchinski and David Milstein

5. Kinetic and Equilibrium Deuterium Isotope Effects for C–H Bond Reductive

Elimination and Oxidative Addition Reactions Involving the

Ansa–Tungstenocene Methyl–Hydride Complex [Me₂Si(C₅Me₄)₂]W(Me)H ....... 86 pdf

Kevin E. Janak, David G. Churchill, and Gerard Parkin

6. Alkane C–H Bond Activation by O-Donor Ir Complexes .................................. 105 pdf

Gaurav Bhalla, Xiang Yang Liu, Antek Wong-Foy, C. J. Jones, and Roy A. Periana

7. Lanthanide Complexes: Electronic Structure and H–H, C–H, and Si–H

Bond Activation from a DFT Perspective ......................................................... 116 pdf

Lionel Perrin, Laurent Maron, and Odile Eisenstein

C–H Bond Activations in Organic Synthesis,

Alkane Dehydrogenation, and Related Chemistry

8. Catalytic, Thermal, Regioselective Functionalization of Alkanes and Arenes

with Borane Reagents ....................................................................................... 136 pdf

John F. Hartwig

9. C–H Bond Functionalization in Complex Organic Synthesis ............................ 155 pdf

Dalibor Sames

10. Pincer and Chelate N-Heterocyclic Carbene Complexes of Rh, Ir and Pd:

Synthetic Routes, Dynamics, Catalysis, Abnormal Binding and

Counterion Effects ............................................................................................. 169 pdf

Anthony R. Chianese and Robert H. Crabtree

11. Sequential Hydrocarbon C–H Bond Activations by 16-Electron

Organometallic Complexes of Molybdenum and Tungsten ............................. 184 pdf

Peter Legzdins and Craig B. Pamplin

12. Alkane Transfer-Dehydrogenation Catalyzed by a Pincer-Ligated

Iridium Complex ................................................................................................ 198 pdf

Alan S. Goldman, Kenton B. Renkema, Margaret Czerw, and Karsten Krogh-Jespersen

13. DFT Calculations on the Mechanism of (PCP)Ir-Catalyzed Acceptorless

Dehydrogenation of Alkanes: Realistic Computational Models and Free

EnergyRelationships ......................................................................................... 216 pdf

Karsten Krogh-Jespersen, Margaret Czerw, and Alan S. Goldman

14. Double Cyclometalation: Implications for Carbon–Hydrogen Oxidative

Addition with PCP Pincer Compounds of Iridium ............................................ 234 pdf

Hani A. Y. Mohammad, Jost C. Grimm, Klaus Eichele, Hans-Georg Mack,

Bernd Speiser, Filip Novak, William C. Kaska, and Hermann A. Mayer

Activation of C–H Bonds by Pt(II) – Shilov Chemistry

15. C–H Bond Activation at Pt(II): A Route to Selective Alkane Oxidation? ....... 250 pdf

Alan F. Heyduk, H. Annita Zhong, Jay A. Labinger, and John E. Bercaw

16. Competitive Trapping of Equilibrating Pt(IV) Hydridoalkyl and Pt(II)

Alkane Complexes: A Valuable Tool for the Mechanistic Investigation of

C‑H Activation Reactions ................................................................................. 264 pdf

Mats Tilset, Lars Johansson, Martin Lersch, and Bror J. Wik

17. Mechanisms of Reactions Related to Selective Alkane Oxidation

by Pt Complexes ................................................................................................ 283 pdf

Jennifer L. Look, Ulrich Fekl, and Karen I. Goldberg

18. Hydrocarbon C–H Bond Activation with Tp'Pt Complexes ............................. 303 pdf

Cynthia M. Norris and Joseph L. Templeton

19. C–H Bond Activation with Neutral Platinum Methyl Complexes .................... 319 pdf

Carl N. Iverson, Charles A. G. Carter, John D. Scollard, Melanie A. Pribisko,

Kevin D. John, Brian L. Scott, R. Tom Baker, John E. Bercaw, and Jay A. Labinger

20. Issues Relevant to C–H Activation at Platinum(II): Comparative Studies

between Cationic, Zwitterionic, and Neutral Platinum(II) Compounds

in Benzene Solution............................................................................................. 334 pdf

Jonas C. Peters, J. Christopher Thomas, Christine M. Thomas, and Theodore A. Betley

Oxidations

21. Non-Organometallic Mechanisms for C–H Bond Oxidation:

Hydrogen Atom vs. Electron vs. Hydride Transfer .......................................... 356 pdf

James M. Mayer, Anna S. Larsen, Jasmine R. Bryant, Kun Wang,

Mark Lockwood, Gordon Rice, and Tae-Jin Won

22. Oxidation of Organic Molecules with Molecular Oxygen

Catalyzed by Heterometallic Complexes .......................................................... 370 pdf

Patricia A. Shapley

23. Catalytic Hydrocarbon Oxidations Involving Coreductants ........................... 379

Joseph E. Remias and Ayusman Sen

24. New Applications of Electrophilic Aromatic C–H Activation

with Metal Trifluoroacetates ............................................................................. 393 pdf

Vladimir V. Grushin, David L. Thorn,

William J. Marshall, and Viacheslav A. Petrov

25. Reengineering of Organic-Based Metal Active Sites

for Oxidations and Oxygenations ..................................................................... 407

Sergiu M. Gorun

Subject Index ....................................................................... 427