Aminoferrocene lithiation by boron trifluoride activation.
Lithiation of BF 3-complexed dimethylaminoferrocene occurs exclusively ortho to the dimethylamino group in the cyclopentadienyl ring providing structurally diverse products in 76-94% yield after electrophile quench. This method represents the first direct C2-lithiation of a monosubstituted aminoferrocene, offering rapid and complementary access to this class of compounds over procedures that utilize carbon- and sulfur-based directing groups and may serve as a prelude to an asymmetric process.
Metallinos
Costa
C
Department of Chemistry, Brock University, 500 Glenridge Avenue, St. Catharines, Ontario L2S 3A1, Canada. cmetallinos@brocku.ca
Zaifman
Josh
J
Dodge
Laura
L