How to Submit
Browse
Events
Communities
About

Copper-Catalyzed Alkynylation of Hydrazides: An Easy Access to Functionalized Azadipeptides

04 August 2022, Version 2
Working Paper
This content is an early or alternative research output and has not been peer-reviewed by Cambridge University Press at the time of posting.

Abstract

We report a copper-catalyzed alkynylation of azadipeptides using ethynylbenziodoxolone (EBX) reagents. Non-symmetrical ynehydrazides could be obtained in 25-97% yield using azaglycine derivatives as nucleophiles. The transfor-mation is compatible with most functional groups naturally occurring on amino acid side-chains and allows the transfer of silyl-, alkyl- and aryl-substituted alkynes. The obtained α-alkynyl azaglycine products could be further functionalized by nucleophilic attack or cycloaddition on the triple bond.

Keywords

peptides
alkynes
hypervalent iodine
copper catalysis
hydrazides
azapeptides

Supplementary materials

Title
Description
Actions
Title
Supporting Information
Description
Experimental procedures, characterization data and copy of NMR spectra.
Actions

Comments

Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting and Discussion Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.

Now Published

Copper-Catalyzed Alkynylation of Hydrazides: An Easy Access to Functionalized Azadipeptides [opens in a new tab]
Eliott Le Du, Julien Borrel, Jerome Waser journal article
Organic Letters , Volume 24, Issue 36
Online publication date: Sep 06, 2022

Version History

Aug 04, 2022 Version 2

Version Notes

Conditions to hydrolyze the hydrazone on functionalized products were added in Scheme 4. The experimental procedure and characterization data for this reaction were added to the SI, and a cover page was added to the SI.

Metrics

1,905
954
0
Views
Downloads
Citations

License

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

DOI

10.26434/chemrxiv-2022-j0x08-v2
D O I: 10.26434/chemrxiv-2022-j0x08-v2 [opens in a new tab]

Funding

Swiss National Science Foundation
200020_182798

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

Share