An Electrochemical Approach for the Synthesis of Perfluoroalkylated Purine and Indole Analogues of Plant Growth Regulators

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-perflu...

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Bibliographic Details
Published inTetrahedron Vol. 56; no. 17; pp. 2655 - 2664
Main Authors Médebielle, Maurice, Fujii, Shozo, Kato, Katsuya
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 21.04.2000
Elsevier
Subjects
Chemistry
Chemistry, Organic
electrochemistry
fluorine and compounds
indole
Physical Sciences
purine
S RN1
Science & Technology
S RN1
indole
electrochemistry
purine
fluorine and compounds
CONVENIENT SYNTHESIS
S(RN)1
TETRAKIS(DIMETHYLAMINO)ETHYLENE
USEFUL REDUCTANT
AROMATIC NUCLEOPHILIC-SUBSTITUTION
SRN1 REACTIONS
HETEROCYCLES
CYTOKININ ACTIVITY
INDUCED S(RN)1 SUBSTITUTION
2,3-DISUBSTITUTED INDOLES
ABSCISIC-ACID
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Summary: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 RN1 mechanism, in moderate to good yields, and biological activity of some of the products was evaluated.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(00)00154-X