Mild chlorodifluoroacylation of indoles via self-activation of sodium chlorodifluoroacetate

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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. © 2014 American Chemical Society.

Bibliographical metadata

Original languageEnglish
Pages (from-to)4024-4027
Number of pages3
JournalOrganic Letters
Issue number15
Publication statusPublished - 1 Aug 2014