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

04 August 2022, Version 2
This content is a preprint and has not undergone peer review 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

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