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Updated: Aug 14, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Concise synthesis of aryl-C-nucleosides by Friedel-Crafts alkylation
Sven Hainke1, Sebastian Arndt, Oliver Seitz
1Humboldt-Universität zu Berlin, Institut für Chemie, Brook-Taylor Str. 2, D-12489, Berlin, Germany.
Abstract:
A fast and simplified synthesis of 1',2'-dideoxy-1'-pyrenyl-riboside and several other C-nucleosides is shown. Shelf-stable 1-O-methyl-3,5-di-O-toluoyl-2-deoxyribose is demonstrated to serve as a versatile glycosyl donor in Lewis acid promoted Friedel-Crafts alkylations of unsubstituted pyrene and other inexpensive arenes such as fluorene and methylnaphthalene. The reaction conditions favour the formation of beta-configurated C-nucleosides which renders additional epimerisation steps unnecessary. As a result, protected beta-aryl-C-nucleosides are available directly from non-substituted arenes in three steps overall.
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