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General, Mild, and Metal‐Free Functionalization of Indole and Its Derivatives Through Direct C3‐Selenylation
Author(s) -
Hałuszczuk Adam,
Babul Natalia,
Nierzwicki Łukasz,
Przychodzeń Witold
Publication year - 2019
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.201900632
Subject(s) - chemistry , indole test , electrophile , reagent , electrophilic substitution , surface modification , ring (chemistry) , cleavage (geology) , combinatorial chemistry , electrophilic aromatic substitution , medicinal chemistry , organic chemistry , stereochemistry , catalysis , geotechnical engineering , fracture (geology) , engineering
A very mild method for the introduction of functionalized alkylselenyl group at C‐3 position of the indole ring was developed. The proposed procedure consists of an electrophilic substitution of indole and its derivatives with bis( O , O ‐diisopropoxyphosphorothioyl) diselenide and subsequent cleavage of the P–Se bond with tetrabutylammonium fluoride in the presence of various electrophilic reagents. This method can be successfully applied, inter alia, for the preparation of amino acid and glucoside derivatives of 3‐selenoindole.