Palladium (II) Catalyze Carbonylation of Ketones

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Journal Title, Volume, Page: 
Tetrahedron Letters Volume 41, Issue 17, Pages 3021–3024
Year of Publication: 
2000
Authors: 
Othman Hamed
Department of Chemistry, Loyola University of Chicago, Chicago, Illinois 60626, USA
Current Affiliation: 
Department of Chemistry, Faculty of Science, An-Najah National University, Nablus, Palestine
Arab El-Qisairi
Department of Chemistry, Loyola University of Chicago, Chicago, Illinois 60626, USA
Patrick M. Henry
Department of Chemistry, Loyola University of Chicago, Chicago, Illinois 60626, USA
Preferred Abstract (Original): 

Cyclic ketones react with PdCl2 in methanol under a CO atmosphere to give mainly diesters by a ring cleavage reaction along with some chloro-substituted monoester. 13CO labeling experiments indicate the major product is formed by a mechanism involving Pd(II)-CO2CH3 insertion across the double bond of the enol form of the ketone. Pd(II) elimination and acid-catalyzed ring cleavage form a second methyl ester group.

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