Application of Organometallic Chemistry – Breaking the Inert C-H Bond Literature Special Topic Date Created by [John Lee, University of Tennessee Chattanooga, [email protected]] and posted on VIPEr (www.ionicviper.org) on [July 16, 2012], Copyright [July, 16, 2012]. This work is licensed under the Creative Commons [Attribution-NonCommercial-ShareAlike 3.0 Unported] License. To view a copy of this license visit http://creativecommons.org/about/license/
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Application of Organometallic Chemistry – Breaking the Inert C-H Bond Literature Special Topic Date Created by [John Lee, University of Tennessee Chattanooga,
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Application of Organometallic Chemistry – Breaking the Inert
C-H Bond
Literature Special Topic
Date
Created by [John Lee, University of Tennessee Chattanooga, [email protected]] and posted on VIPEr (www.ionicviper.org) on [July 16, 2012], Copyright [July, 16, 2012]. This work is licensed under the Creative Commons [Attribution-NonCommercial-ShareAlike 3.0 Unported] License. To view a copy of this license visit http://creativecommons.org/about/license/
You want to break which bond!
-Why do we draw line structures forOrganic molecules?
-High bond energymethane 100 kcal/molbenzene 110 kcal/mol
-High pKaon the order of >40
**,but…Nature uses the C-H bond: See methane monooxygenase and vitamin-b12
Example Organic Molecules
In organic chemistry….
Carey, F. A. Organic Chemistry, 4th ed. 2001, McGraw-Hill, Chapter 8.
Leaving Groups (LG)
Generic Substitution Reaction (SN1 shown)
TsO-, NH3 > I-, H2O > Br- > Cl- > HO-, NH2-, RO-
Heck, R. F.; Negishi, E.; Suzuki, A. palladium catalyzed cross couplings in Organic Synthesis: Great Art in a Test Tube.http://nobelprize.orglnobeljrizes/chemistry/laureatesl}O10/press.html (March 17, 2011).
In organometallic chemistry….
Cross-Coupling Reactions
but wait I said C-H not C-X activation?
If it ain’t broke why fix it?If it ain’t broke why fix it?
-Nearly everything comes from coal, oil or natural gasCoal: 1,000 – 2,000 yearsOil: 50 – 150 yearsNatural gas: 207 – 590 years
-However this is not sustainable for population growthWhy?
-We are a good 10-20 (optimistic) years from solar
-For the interim time we should use our resources to the best of our ability
How?
Lewis, N. S.; Nocera, D. G. Proc. Nat. Acad. Sci. 2006, 103,