Iron-assisted nucleophilic aromatic substitution on solid phase.
Iron-assisted S(N)Ar reactions were performed for the first time on solid phase, and a library of 36 unsymmetrically substituted phenylpiperazines and phenyl-1,4-diazepanes was synthesized with this novel strategy. The scope of iron-assisted S(N)Ar reactions on solid phase was investigated, and reactions of representative nucleophiles from groups VI (O, S, and Se) and V (N and P) of the periodic table were examined. Decomplexation of resin-bound iron complexes was achieved with 1,10-phenanthroline under irradiation, thereby overcoming the notorious disadvantages of decomplexation observed in solution-phase chemistry.
Department of Combinatorial Chemistry, Medicinal Chemistry Research, H. Lundbeck A/S, 9 Ottiliavej, DK-2500 Valby, Denmark. tr@lundbeck.com
Thomas
T
Ruhland
Kia S
KS
Bang
Kim
K
Andersen