Carbofluorination via a palladium-catalyzed cascade reaction

Marie Gabrielle Braun, Matthew H. Katcher, Abigail G. Doyle

Research output: Contribution to journalArticlepeer-review

55 Scopus citations

Abstract

This article demonstrates the first examples of tandem C-C and C-F bond formation for the palladium-catalyzed carbofluorination of allenes. The intramolecular Heck-fluorination cascade provides monofluoromethylated heteroarenes, an important class of products in medicinal chemistry. We also describe an intermolecular variant for the three-component coupling of allenes, aryl iodides, and AgF. Mechanistic studies indicate that C-F bond formation occurs by outer sphere attack of fluoride on an allylpalladium fluoride intermediate.

Original languageEnglish (US)
Pages (from-to)1216-1220
Number of pages5
JournalChemical Science
Volume4
Issue number3
DOIs
StatePublished - Feb 4 2013

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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