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Issue 14, 2019
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A straightforward and versatile FeCl3 catalyzed Friedel–Crafts C-glycosylation process. Application to the synthesis of new functionalized C-nucleosides

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Abstract

A new, straightforward and eco-compatible route to C-(hetero)aryl nucleosides is reported. This ribosylation process consists of a one-step FeCl3 catalyzed Friedel–Crafts β-C-glycosydation reaction. This reaction occurs through an oxonium intermediate from readily available protected sugars leading to functionalized C-nucleosides with high stereocontrol. The expected new C-nucleosides were obtained in good yields within a short reaction time (10 min). Moreover, this approach is compatible with the use of a range of bulky (poly)aromatics such as naphthalene, anthracene and pyrene, which are not easily accessible via classical routes. These new C-aryl-nucleosides exhibit interesting photophysical properties, underling their potential use for further nucleic acid labelling.

Graphical abstract: A straightforward and versatile FeCl3 catalyzed Friedel–Crafts C-glycosylation process. Application to the synthesis of new functionalized C-nucleosides

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Supplementary files

Article information


Submitted
13 Dec 2018
Accepted
06 Mar 2019
First published
11 Mar 2019

New J. Chem., 2019,43, 5551-5558
Article type
Paper

A straightforward and versatile FeCl3 catalyzed Friedel–Crafts C-glycosylation process. Application to the synthesis of new functionalized C-nucleosides

H. Tachallait, M. Safir Filho, H. Marzag, K. Bougrin, L. Demange, A. R. Martin and R. Benhida, New J. Chem., 2019, 43, 5551
DOI: 10.1039/C8NJ06300A

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