Regiocontrolled synthesis of carbocycle-fused indoles via arylation of silyl enol ethers with o-nitrophenylphenyliodonium fluoride.
[formula: see text] A new, regiocontrolled synthesis of carbocycle-fused indoles has been developed. The two-step procedure involves first the regiospecific arylation of silyl enol ethers with o-nitrophenylphenyliodonium fluoride (1). Reduction of the nitro group on the aromatic ring with TiCl3 followed by spontaneous condensation of the aniline with the ketone then affords the indole products.
Iwama
T
T
Department of Chemistry, University of Chicago, Illinois 60637, USA.
Birman
V B
VB
Kozmin
S A
SA
Rawal
V H
VH
D007211:Indoles / Q000138:chemical synthesis*; D007462:Iodobenzenes / Q000138:chemical synthesis* / Q000737:chemistry; D009578:Nitrobenzenes / Q000138:chemical synthesis* / Q000737:chemistry
D007211:Indoles; D007462:Iodobenzenes; D009578:Nitrobenzenes; C410466:2-nitrophenylphenyliodonium