title: Mild chlorodifluoroacylation of indoles via self-activation of sodium chlorodifluoroacetate.
abstract: A mild acylation of N-alkylindoles is reported using sodium chlorodifluoroacetate (SCDA) to synthesize useful chlorodifluoroketones. Friedel-Crafts reactivity of carboxylate salts is unusual and is not observed in similar electron-deficient acetate salts such as sodium trifluoroacetate. Mechanistic experiments indicate that the characteristic ability of SCDA to generate difluorocarbene is responsible for the reaction pathway via self-activation to form the active ester.
authors.affiliation: School of Chemistry, University of Manchester , Oxford Road, Manchester M13 9PL, U.K.
authors.forename: Thomas J
authors.initials: TJ
authors.lastname: Williams
authors.forename: Michael F
authors.initials: MF
authors.lastname: Greaney