Palladium-catalyzed asymmetric synthesis of allylic fluorides

Matthew H. Katcher, Abigail G. Doyle

Research output: Contribution to journalArticle

138 Scopus citations

Abstract

The enantioselective fluorination of readily available cyclic allylic chlorides with AgF has been accomplished using a Pd(0) catalyst and Trost bisphosphine ligand. The reactions proceed with unprecedented ease of operation for Pd-mediated nucleophilic fluorination, allowing access to highly enantioenriched cyclic allylic fluorides that bear diverse functional groups. Evidence that supports a mechanism in which C-F bond formation occurs by an SN2-type attack of fluoride on a Pd(II)-allyl intermediate is presented.

Original languageEnglish (US)
Pages (from-to)17402-17404
Number of pages3
JournalJournal of the American Chemical Society
Volume132
Issue number49
DOIs
StatePublished - Dec 15 2010

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint Dive into the research topics of 'Palladium-catalyzed asymmetric synthesis of allylic fluorides'. Together they form a unique fingerprint.

  • Cite this