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Ligand-Free Iron-Catalyzed C-F Amination of Diarylamines: A One-Pot Regioselective Synthesis of Diaryl Dihydrophenazines

Research output: Contribution to journalArticle

  • Yuma Aoki
  • Harry M. O'Brien
  • Hiroto Kawasaki
  • Hikaru Takaya
  • Masaharu Nakamura
Original languageEnglish
Pages (from-to)461-464
Number of pages4
JournalOrganic Letters
Volume21
Issue number2
Early online date10 Jan 2019
DOIs
DateAccepted/In press - 10 Jan 2019
DateE-pub ahead of print - 10 Jan 2019
DatePublished (current) - 18 Jan 2019

Abstract

A one-pot synthesis of various 5,10-diaryl-5,10-dihydrophenazines (DADHPs) from diarylamines has been achieved by using an iron-catalyzed C-F amination. Homodimerization of magnesium diarylamides, followed by defluorinative intramolecular cyclization (double ortho C-F amination) in the presence of catalytic FeCl2 and stoichiometric 1,2-dibromoethane, affords the corresponding DADHPs with complete regiocontrol. The unique high reactivity of fluorine over other halogens indicates that amination proceeds via an SNAr mechanism facilitated by iron.

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