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Reactions of Arynes with Nitrosoarenes—An Approach to Substituted Carbazoles
Author(s) -
Chakrabarty Shyamal,
Chatterjee Indranil,
Tebben Ludger,
Studer Armido
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201209447
Subject(s) - aryne , trifluoromethanesulfonate , dimethoxyethane , chemistry , fluoride , solvent , combinatorial chemistry , organic chemistry , medicinal chemistry , computational chemistry , catalysis , inorganic chemistry , electrode , electrolyte
No transition metals are necessary in the reaction of in situ generated arynes with nitrosoarenes to give substituted carbazoles. Depending on the fluoride source and the solvent, either N‐arylated carbazoles or NH‐carbazoles are obtained (see scheme; DME=dimethoxyethane, OTf=trifluoromethanesulfonate). In these cascades a CC and one or two CN bonds are formed. The reactions are easy to conduct and proceed under mild conditions.