title: Silver-promoted, palladium-catalyzed direct arylation of cyclopropanes: facile access to spiro 3,3'-cyclopropyl oxindoles.
abstract: 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.
authors: Centre in Green Chemistry and Catalysis, Department of Chemistry, Université de Montréal, P.O. Box 6128 Station Downtown, Montréal, Québec, H3C 3J7, Canada.
authors: Carolyn L
authors: CL
authors: Ladd
authors: Daniela
authors: D
authors: Sustac Roman
authors: André B
authors: AB
authors: Charette
mesh_terms: D002384:Catalysis; D003521:Cyclopropanes / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D000078183:Oxindoles; D010165:Palladium / Q000737:chemistry*; D012834:Silver / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D003521:Cyclopropanes; D007211:Indoles; D000078183:Oxindoles; D013141:Spiro Compounds; C022960:2-oxindole; D012834:Silver; D010165:Palladium