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Copper‐Catalyzed Trifluoromethylation of Aliphatic N ‐Arylhydrazones: A Concise Synthetic Entry to 2‐Trifluoromethylindoles from Simple Aldehydes
Author(s) -
Prieto Alexis,
Landart Mélissa,
Baudoin Olivier,
Monteiro Nuno,
Bouyssi Didier
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500237
Subject(s) - trifluoromethylation , chemistry , hydrazone , reagent , aldehyde , catalysis , indole test , copper , combinatorial chemistry , organic chemistry , trifluoromethyl , alkyl
The copper‐catalyzed C( sp 2 )H trifluoromethylation of N,N ‐disubstituted hydrazones using the Togni reagent is demonstrated to proceed efficiently for aliphatic aldehyde‐derived substrates. The success of the reactions relied on the choice of the N,N ‐diphenylamino group as the terminal hydrazone amino group where N,N ‐dialkylamino groups were preferred for (hetero)aromatic aldehyde‐derived substrates. In addition, the trifluoromethylated N ‐arylhydrazones are shown to be ideal substrates for Fischer indole synthesis allowing a straightforward, three‐step access to 2‐trifluoromethylindole derivatives from simple aldehydes.