Premium
Facile Synthesis of Trisubstituted Carbazoles by Acid‐Catalyzed Ring‐Opening Annulation of 2‐Amidodihydrofurans with Indoles
Author(s) -
Zhao Jingjing,
Li Pan,
Xia Chungu,
Li Fuwei
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201503260
Subject(s) - annulation , regioselectivity , chemistry , chemoselectivity , ring (chemistry) , catalysis , trifluoromethanesulfonate , trimethylsilyl , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry
Abstract A mild and convenient synthesis of carbazoles by TfOTMS (trimethylsilyl trifluoromethanesulfonate)‐catalyzed ring‐opening annulation of 2‐amidodihydrofurans is presented with a high degree of chemoselectivity and regioselectivity. This procedure was also scaled up to a gram‐scale synthesis. The reaction could involve an iminonium intermediate through a series of CO, CN bond cleavages, CC bond formations, and a 1,2‐migration process.