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Transient imine as a directing group for the Pd-catalyzed anomeric C(sp)3-H arylation of 3-aminosugars

29 December 2022, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The first example of Pd(II)-catalyzed anomeric arylation of 3-aminosugars is reported by using an L,X-type transient directing groups (TDG) approach combined with an external 2-pyridone ligand. The released free amine was in situ transformed into an azide function, which was then exploited in a CuAAC to increase the molecular complexity and prepare a variety of complex substituted C3-triazolo C-glycosides in good yields.

Keywords

Aryl C-Glycosides
C-H activation
Transient directing group

Supplementary materials

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Description
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Supplementary Materials
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Synthesis Procedures, RMN data, RX data, DFT calculations, NMR spectra
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Version History

Dec 29, 2022 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2022-fwgr0
D O I: 10.26434/chemrxiv-2022-fwgr0 [opens in a new tab]

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

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