ol8b03848_si_001.pdf (5.69 MB)
Metal-Free C–H Functionalization and Aromatization Sequence for the Synthesis of 1‑(Indol-3-yl)carbazoles and Total Synthesis of 7‑Bromo-1-(6-bromo‑1H‑indol-3-yl)‑9H‑carbazole
journal contribution
posted on 2019-01-23, 22:15 authored by Ganapathy Ranjani, Rajagopal NagarajanAn
operationally simple, metal-free, cost-effective, and mild oxidative
cross-coupling protocol for the synthesis of 1-indolyl tetrahydrocarbazoles
to afford 1-(indol-3-yl)carbazoles is developed. N-Chlorosuccinimide is used as a mild oxidant for the functionalization
of the 1-position of tetrahydrocarbazoles, aromatization of which
furnished 1-(indol-3-yl)carbazoles in good to moderate yields without
employing protection/deprotection strategy. A naturally rare dibromo
1-(indol-3-yl)carbazole alkaloid was synthesized for the first time
in two steps with an overall yield of 64% by applying the same methodology.