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Issue 28, 2018
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Palladium catalyzed stereocontrolled synthesis of C-aryl glycosides using glycals and arenediazonium salts at room temperature

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Abstract

A stereocontrolled synthesis of aryl-C-glycosides was achieved using glycals and aryldiazonium salts in the presence of palladium acetate. A wide range of glycals including D-glucal, D-galactal, L-rhamnal, D-xylal and D-ribal underwent C-arylation at the anomeric carbon in the presence of different aryldiazonium tetrafluoroborates and gave synthetically useful 2,3-deoxy-3-keto-α-aryl-C-glycosides in good to excellent yields. Broad substrate scope, simple operation and room temperature reactions make this protocol very attractive in organic synthesis.

Graphical abstract: Palladium catalyzed stereocontrolled synthesis of C-aryl glycosides using glycals and arenediazonium salts at room temperature

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Publication details

The article was received on 12 Jun 2018, accepted on 27 Jun 2018 and first published on 28 Jun 2018


Article type: Communication
DOI: 10.1039/C8OB01393D
Citation: Org. Biomol. Chem., 2018,16, 5107-5112
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    Palladium catalyzed stereocontrolled synthesis of C-aryl glycosides using glycals and arenediazonium salts at room temperature

    A. K. Singh and J. Kandasamy, Org. Biomol. Chem., 2018, 16, 5107
    DOI: 10.1039/C8OB01393D

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