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Facile Synthesis of 2‐(Perfluoroalkyl)indoles through a Michael Addition/Cu I ‐Catalyzed Annulation Process
Author(s) -
Cao Long,
Shen Dandane,
Wei Jiamei,
Chen Jie,
Deng Hongmei,
Shao Min,
Shi Jumei,
Zhang Hui,
Cao Weiguo
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201400056
Subject(s) - annulation , chemistry , catalysis , michael reaction , indole test , functional group , organic chemistry , copper , medicinal chemistry , combinatorial chemistry , polymer
A practical and economical process for the synthesis of perfluoroalkylated indole compounds has been developed. The Michael addition of 2‐iodo‐ or 2‐bromoanilines to methyl perfluoroalk‐2‐ynoates affords N ‐( o ‐haloaryl)enamines, which subsequently undergo a copper‐catalyzed annulation reaction to give 2‐perfluoroalkyl‐substituted indoles in good to excellent yields. This method displays excellent functional group tolerance and is carried out in one pot under mild conditions.