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Silver-promoted, palladium-catalyzed direct arylation of cyclopropanes: facile access to spiro 3,3'-cyclopropyl oxindoles.
Org Lett. 2013 Mar 15; 15(6):1350-3.OL

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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Publisher Full Text (DOI)

Authors+Show Affiliations

Ladd CL
Centre in Green Chemistry and Catalysis, Department of Chemistry, Université de Montréal, P.O. Box 6128 Station Downtown, Montréal, Québec, H3C 3J7, Canada.
Sustac Roman D
No affiliation info available
Charette AB
No affiliation info available

MeSH

CatalysisCyclopropanesIndolesMolecular StructureOxindolesPalladiumSilverSpiro Compounds

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

23452033

Citation

Ladd, Carolyn L., et al. "Silver-promoted, Palladium-catalyzed Direct Arylation of Cyclopropanes: Facile Access to Spiro 3,3'-cyclopropyl Oxindoles." Organic Letters, vol. 15, no. 6, 2013, pp. 1350-3.
Ladd CL, Sustac Roman D, Charette AB. Silver-promoted, palladium-catalyzed direct arylation of cyclopropanes: facile access to spiro 3,3'-cyclopropyl oxindoles. Org Lett. 2013;15(6):1350-3.
Ladd, C. L., Sustac Roman, D., & Charette, A. B. (2013). Silver-promoted, palladium-catalyzed direct arylation of cyclopropanes: facile access to spiro 3,3'-cyclopropyl oxindoles. Organic Letters, 15(6), 1350-3. https://doi.org/10.1021/ol4003338
Ladd CL, Sustac Roman D, Charette AB. Silver-promoted, Palladium-catalyzed Direct Arylation of Cyclopropanes: Facile Access to Spiro 3,3'-cyclopropyl Oxindoles. Org Lett. 2013 Mar 15;15(6):1350-3. PubMed PMID: 23452033.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Silver-promoted, palladium-catalyzed direct arylation of cyclopropanes: facile access to spiro 3,3'-cyclopropyl oxindoles. AU - Ladd,Carolyn L, AU - Sustac Roman,Daniela, AU - Charette,André B, Y1 - 2013/03/01/ PY - 2013/3/5/entrez PY - 2013/3/5/pubmed PY - 2013/7/25/medline SP - 1350 EP - 3 JF - Organic letters JO - Org Lett VL - 15 IS - 6 N2 - 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. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/23452033/Silver_promoted_palladium_catalyzed_direct_arylation_of_cyclopropanes:_facile_access_to_spiro_33'_cyclopropyl_oxindoles_ L2 - https://doi.org/10.1021/ol4003338 DB - PRIME DP - Unbound Medicine ER -