Photocatalyzed reductive fluoroalkylation of 2-acetoxyglycals towards the stereoselective synthesis of α-1-fluoroalkyl- C -glycosyl derivatives

A benign, efficient, regio- and stereoselective protocol for the syntheses of α-1-fluoroalkyl-C-glycosyl compounds bearing CF3, C4F9, and C6F13 substituents on the anomeric carbon has been developed by a new methodology starting from 2-acetoxyglycals for the first time. Remarkably, the reactions pro...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2020-11, Vol.18 (42), p.8724-8734
Main Authors: Mora Flores, Erwin W, Uhrig, María Laura, Postigo, Al
Format: Article
Language:English
Subjects:
Iodides
Mathematical analysis
NMR
Nuclear magnetic resonance
Stereoselectivity
Substrates
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Summary:A benign, efficient, regio- and stereoselective protocol for the syntheses of α-1-fluoroalkyl-C-glycosyl compounds bearing CF3, C4F9, and C6F13 substituents on the anomeric carbon has been developed by a new methodology starting from 2-acetoxyglycals for the first time. Remarkably, the reactions proceeded in only one step, through the visible light-photocatalyzed reductive fluoroalkylation of 2-acetoxyglycals by means of an Ir photocatalyst and employed commercially available fluoroalkyl iodides n-CnF2n+1-I (n = 1, 4, 6) as a source of fluoroalkyl radicals.
ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob01914c