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Issue 23, 2019
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Copper-mediated anomeric O-arylation with organoboron reagents

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Abstract

Copper-mediated couplings of arylboroxines with glycosyl hemiacetals furnish O-aryl glycosides via Csp2–O bond formation. The method enables the anomeric O-arylation of protected pyranose and furanose derivatives, and is tolerant of functionalized arylboroxine partners. Whereas mixtures of anomers are formed from glucopyranose, galactopyranose and arabinofuranose hemiacetals, the α-anomer is generated selectively from mannopyranose and mannofuranose-derived substrates.

Graphical abstract: Copper-mediated anomeric O-arylation with organoboron reagents

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Publication details

The article was received on 03 May 2019, accepted on 16 May 2019 and first published on 24 May 2019


Article type: Communication
DOI: 10.1039/C9OB01022J
Org. Biomol. Chem., 2019,17, 5671-5674

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    Copper-mediated anomeric O-arylation with organoboron reagents

    V. Dimakos, J. J. W. Liu, Z. Ge and M. S. Taylor, Org. Biomol. Chem., 2019, 17, 5671
    DOI: 10.1039/C9OB01022J

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