Metal-catalyzed benzylic fluorination as a synthetic equivalent to 1,4-conjugate addition of fluoride.
We explore in detail the iron-catalyzed benzylic fluorination of substrates containing aromatic rings and electron-withdrawing groups positioned β to one another, thus providing direct access to β-fluorinated adducts. This operationally convenient process can be thought of not only as a contribution to the timely problem of benzylic fluorination but also as a functional equivalent to a conjugate addition of fluoride, furnishing products in moderate to good yields and in excellent selectivity.
Department of Chemistry, Johns Hopkins University , 3400 North Charles Street, Baltimore, Maryland 21218, United States.
Steven
S
Bloom
Seth Andrew
SA
Sharber
Maxwell Gargiulo
MG
Holl
James Levi
JL
Knippel
Thomas
T
Lectka