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

Yuma Aoki, Harry M. O'Brien, Hiroto Kawasaki, Hikaru Takaya, Masaharu Nakamura*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

5 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)461-464
Number of pages4
JournalOrganic Letters
Volume21
Issue number2
Early online date10 Jan 2019
DOIs
Publication statusPublished - 18 Jan 2019

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