Issue 23, 2019

Copper-mediated anomeric O-arylation with organoboron reagents

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

Supplementary files

Article information

Article type
Communication
Submitted
03 May 2019
Accepted
16 May 2019
First published
24 May 2019

Org. Biomol. Chem., 2019,17, 5671-5674

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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