☆ 4.8 Article

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

ORGANIC LETTERS (2013)

Journal

ORGANIC LETTERS

Volume 15, Issue 6, Pages 1350-1353

Publisher

AMER CHEMICAL SOC

DOI: 10.1021/ol4003338

Keywords

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Categories

Chemistry, Organic

Funding

Universite de Montreal
Natural Science and Engineering Council of Canada (NSERC)
Centre in Green Chemistry and Catalysis
Canada Research Chair Program
Canada Foundation for Innovation
NSERC

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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.

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