1‑Iodoglycal: A Versatile Intermediate for the Synthesis of d‑Glyco Amides and Esters Employing Carbonylative Cross-Coupling Reaction

In this study, we present the development of two catalytic processes: a Pd-PEPPSI-catalyzed aminocarbonylation and a Pd­(OAc)2-Xantphos-catalyzed alkoxycarbonylation of d-glycals, utilizing carbonylative cross-coupling reactions. We explored successfully various types of aromatic amines, as well as...

Full description

Saved in:
Bibliographic Details
Published in:ACS omega 2024-07, Vol.9 (29), p.31732-31744
Main Authors: Hornink, Milene M., Toledo, Monica F. Z. J., Pimenta, Daniel C., Paschoalin, Caio, Silva, Pamela M., Figlino, Giuseppe E., Aguiar, Eurípedes, Cervi, Gustavo, Ribeiro, Francisco W. M., Carita Correra, Thiago, Ferry, Angélique, Stefani, Hélio A.
Format: Article
Language:English
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:In this study, we present the development of two catalytic processes: a Pd-PEPPSI-catalyzed aminocarbonylation and a Pd­(OAc)2-Xantphos-catalyzed alkoxycarbonylation of d-glycals, utilizing carbonylative cross-coupling reactions. We explored successfully various types of aromatic amines, as well as alkyl amines and amino acids, to synthesize new d-glycal amides. However, we observed limitations in the reactivity of alkyl and heteroaromatic amines. The processes enabled the synthesis of 20 novel C1-branched glycoamides and 7 new d-gluco esters.
ISSN:2470-1343
2470-1343
DOI:10.1021/acsomega.4c02645