title: Ylide mediated carbonyl homologations for the preparation of isatin derivatives.
abstract: An exceptionally mild method for the preparation of isatin derivatives has been developed using a sulfur ylide mediated carbonyl homologation sequence starting from anthranilic acid precursors. This method proceeds at ambient temperature via a sulfur ylide intermediate without the need for protection of the amine or chromatographic isolation of the intermediate ylide. Gentle oxidation of the sulfur ylides provides isatin derivatives with N-H, N-alkyl, N-aryl substitution, electron-rich and electron-poor aromatic rings, and heterocyclic aromatic systems. We anticipate that this method will greatly expand the accessibility of complex isatin derivatives.
authors.affiliation: Department of Chemistry, Southern Methodist University, Dallas, TX 75275-0314, USA. alippert@smu.edu.
authors.forename: Christina T
authors.initials: CT
authors.lastname: Lollar
authors.forename: Katherine M
authors.initials: KM
authors.lastname: Krenek
authors.forename: Kevin J
authors.initials: KJ
authors.lastname: Bruemmer
authors.forename: Alexander R
authors.initials: AR
authors.lastname: Lippert
mesh_terms: D007510:Isatin / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D007510:Isatin