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Cu‐Catalyzed Carbenoid Functionalization of Indoles by Methyl 3,3,3‐Trifluoro‐2‐diazopropionate
Author(s) -
Tsyshchuk Irina E.,
Vorobyeva Daria V.,
Peregudov Alexander S.,
Osipov Sergey N.
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.201301734
Subject(s) - chemistry , carbenoid , surface modification , indole test , regioselectivity , catalysis , carbene , trifluoromethyl , carboxylate , combinatorial chemistry , stereochemistry , organic chemistry , rhodium , alkyl
An efficient protocol for the direct CH‐functionalization of indole and its derivatives has been developed by using Cu(F 3 ‐acac) 2 ‐catalyzed insertion of CF 3 ‐carbene derived from methyl 3,3,3‐trifluoro‐2‐diazopropionate. The reaction proceeds with high regioselectivity within a few minutes under low catalyst loading and allows the introduction of CF 3 and carboxylate functions simultaneously into the 3‐ or 2‐position of the indole core. This method can be successfully applied for the synthesis of trifluoromethyl‐containing paullones, which are new members of the known family of potent inhibitors of cyclin‐dependent kinases.