Organic Chemistry Seminar - - NOTE TIME CHANGE

Thursday, October 6, 2011

4:00pm to 5:00pm

Noyes 153 (J. Holmes Sturdivant Lecture Hall)

Asymmetric Pd-NHC*-Catalyzed Coupling Reactions

Peter Kundig, professor of organic chemistry, Department of Organic Chemistry, University of Geneva,

ASYMMETRIC Pd-NHC*-CATALYZED COUPLING REACTIONS

Peter Kündig

Department of Organic Chemistry, University of Geneva 30 Quai Ernest Ansermet CH-1211 Geneva, Switzerland E-mail: [email protected]

Very high asymmetric inductions result in the palladium catalyzed intramolecular arylation of amides to give 3,3-disubstituted oxindoles when new in-situ generated chiral N-heterocyclic carbenes are employed. Structural studies show that conformational locking to avoid allylic strain is the key for understanding the role of the different elements in these ligands.1 The same ligands find applications in the area of asymmetric coupling reactions involving C(sp3)-H bonds. Hghly enantioenriched fused indolines are accessible using either preformed- or in situ-generated Pd-NHC* catalysts. Remarkably, this occurs at high temperature (140-160 C) via excellent asymmetric recognition of an enantiotopic C-H bond in an unactivated methylene unit.2

1. Jia, Y.-X.; Katayev, D.; Seidel, T. M.; Bernardinelli, G.; Kündig E. P., Chem. Eur. J. 2010, 16, 6300 6309 and ref cit. 2. Nakanishi, M.; Katayev, D.; Besnard, C.; Kündig, E. P. Angew. Chem. Int. Ed. 2011, 50, 7438-7441.

For more information, please contact Arleen (Lynne) Martinez by phone at 4004 or by email at [email protected].

Event Series

Organic Chemistry Seminar Series

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