Regiocontrolled synthesis of carbocycle-fused indoles via arylation of silyl enol ethers with o-nitrophenylphenyliodonium fluoride

Authors
Iwama, T Birman, VB Kozmin, SA Rawal, VH
Citation
T. Iwama et al., Regiocontrolled synthesis of carbocycle-fused indoles via arylation of silyl enol ethers with o-nitrophenylphenyliodonium fluoride, ORG LETT, 1(4), 1999, pp. 673-676
Citations number
34
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
4
Year of publication
1999
Pages
673 - 676
Database
ISI
SICI code
1523-7060(19990826)1:4<673:RSOCIV>2.0.ZU;2-M
Abstract
A new, regiocontrolled synthesis of carbocycle-fused indoles has been devel oped. 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 product s.