TY - JOUR
T1 - Ligand-Free Iron-Catalyzed C-F Amination of Diarylamines
T2 - A One-Pot Regioselective Synthesis of Diaryl Dihydrophenazines
AU - Aoki, Yuma
AU - O'Brien, Harry M.
AU - Kawasaki, Hiroto
AU - Takaya, Hikaru
AU - Nakamura, Masaharu
PY - 2019/1/18
Y1 - 2019/1/18
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85060086844&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.8b03702
DO - 10.1021/acs.orglett.8b03702
M3 - Article (Academic Journal)
C2 - 30628796
AN - SCOPUS:85060045949
VL - 21
SP - 461
EP - 464
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 2
ER -