General, Mild, and Metal‐Free Functionalization of Indole and Its Derivatives Through Direct C3‐Selenylation. Issue 27 (24th June 2019)

• Record Type: Journal Article
• Authors: Hałuszczuk, Adam; Babul, Natalia; Nierzwicki, Łukasz; Przychodzeń, Witold
• Is Part Of: European journal of organic chemistry. Issue 27(2019)
• Page Start: 4411
• Page End: 4416
• Publication Date: 2019-06-24
• Subjects: Selenium -- Phosphorus -- Heterocycles -- Aromatic substitution -- Protecting groups; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201900632
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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. Abstract : A nature‐mimicking synthetic route enables the preparation of C‐3 indoyl selenoethers bearing labile functionalized alkyl substituents on the selenium atom.