Copper-mediated anomeric O-arylation with organoboron reagents

Victoria Dimakos; Jacklyn J. W. Liu; Zhenlu Ge; Mark S. Taylor

doi:10.1039/C9OB01022J

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Copper-mediated anomeric O-arylation with organoboron reagents†

Victoria Dimakos,^a Jacklyn J. W. Liu,^a Zhenlu Ge^a and Mark S. Taylor

*^a

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* Corresponding authors

^a Department of Chemistry, University of Toronto, 80 St. George St., Toronto, ON, M5S 3H6 Canada
E-mail: mtaylor@chem.utoronto.ca

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.

This article is part of the themed collections: Chemical Biology in OBC and Trends in Organoboron Chemistry

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Article information

DOI: https://doi.org/10.1039/C9OB01022J
Article type: Communication
Submitted: 03 May 2019
Accepted: 16 May 2019
First published: 24 May 2019

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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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Organic & Biomolecular Chemistry

Copper-mediated anomeric O-arylation with organoboron reagents†

Abstract

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Copper-mediated anomeric O-arylation with organoboron reagents

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