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Silver-Promoted, Palladium-Catalyzed Direct Arylation of Cyclopropanes: Facile Access to Spiro 3,3′-Cyclopropyl Oxindoles

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posted on 2013-03-15, 00:00 authored by Carolyn L. Ladd, Daniela Sustac Roman, André B. Charette
The Pd-catalyzed, Ag(I)-mediated intramolecular direct arylation of cyclopropane C–H bonds is described. Various spiro 3,3′-cyclopropyl oxindoles can be obtained in good to excellent yields from easily accessible 2-bromoanilides. The kinetic isotope effect was determined and epimerization studies were conducted, suggesting that the formation of a putative Pd-enolate is not operative and that the reaction proceeds via a C–H arylation pathway.

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