Chemistry 436 » Spring » 1st Half
2 Credits
Applications of Organometallic Chemistry to Synthesis
Instructor(s): Robert K. Boeckman, Jr.Prerequisites: CHM 421.
Crosslisting: None.
Course Summary:
The transition metal mediated organometallic reactions most commonly employed in organic synthesis will be discussed including their substrate scope, mechanism, and stereo- and/or regiochemical course. Emphasis will be placed on the practical aspects such as catalyst and reaction condition selection, and protocols for trouble shooting catalytic cycles.
The transition metal mediated organometallic reactions most commonly employed in organic synthesis will be discussed including their substrate scope, mechanism, and stereo- and/or regiochemical course. Emphasis will be placed on the practical aspects such as catalyst and reaction condition selection, and protocols for trouble shooting catalytic cycles.
Course Topics:
- Basic Reaction Types
- Mechanisms
- Key Features
- Cross Coupling Reactions
- C-C Bond Forming Reactions: Kumada, Stille, Suzuki, Sonogashira
- Heteroatom-C Cross Coupling Reactions: Amination C-N Coupling (Pd, Ni); Cu Catalyzed Amidation; Cu
- Catalyzed N-Vinylation; Cu Catalyzed Amination; Pd Catalyzed O-C and S-C Coupling
- Heck Reaction: Mechanism, Regioselectivity, Stereoselectivity; Catalyst Systems; Functional Group
- Compatibility; Matsuda-Heck Reaction and Other Variations; Additives, Experimental Modifications;
- Examples & Applications; Asymmetric Heck Reaction
- Other Metal Catalyzed Addition Reactrions
- π-Allyl Palladium Chemistry
- Mechanism, Regiochemistry, Stereochemistry
- Examples
- Asymmetric π-Allylpalladium reactions
- Olefin Metathesis
Required Text:
Transition Metals in the Synthesis of Complex Organic Molecules, 2nd Ed., Hegedus, L. S. University Science Books, 1999, 337pp.
Reference Texts:
Principles and Applications of Organotransition Metal Chemistry, 2nd Ed., Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G., University Science Books, 1987, 989pp.
Palladium Reagents in Organic Synthesis, Tsuji, J., John Wiley & Sons 1996.
Transition Metals in the Synthesis of Complex Organic Molecules, 2nd Ed., Hegedus, L. S. University Science Books, 1999, 337pp.
Reference Texts:
Principles and Applications of Organotransition Metal Chemistry, 2nd Ed., Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G., University Science Books, 1987, 989pp.
Palladium Reagents in Organic Synthesis, Tsuji, J., John Wiley & Sons 1996.