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Electrophilic substitution of indole with trifluoroacetaldehyde hemiaminals 1a-f, prepared from primary amines and trifluoroacetaldehyde ethyl hemiacetal (TFAE), proceeds readily in the presence of Lewis acids. Formation of N-alkyl 1-(indol-3-yl)-2,2,2-trifluoroethylamines (2) is preferred in the presence of BF 3 , but yield of 2,2,2-trifluoroethyl alcohol (3) markedly increases when ZnI ...
In an effort to prepare new fluorine-containing molecules as analogues of Plant Growth Regulators (PGRs), the indirect electrochemical reduction, by means of an aromatic anion mediator, of perfluoroalkyl halides in the presence of purine and indolyl anions was carried out. The corresponding C-perfluoroalkylated products were obtained by an S RN 1 mechanism, in moderate to good yields,...
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