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- Title
Synthesis of Diverse C2‐Glyco‐Acyl Azides and ‐Ureas by Palladium‐Catalyzed Carbonylation Coupling of 2‐Iodoglycals.
- Authors
Soares‐Paulino, Antônio Augusto; Stefani, Hélio A.
- Abstract
Herein, we describe the synthesis of acyl azides and acyl urea glycals, a new class of C‐2 branched glycoconjugates, employing Pd‐catalyzed carbonylative coupling. A new strategy was developed to obtain acyl azides by carbonylative coupling between 2‐iodo‐glycals and NaN3 catalyzed by Pd(dba)2/Xantphos and carbon monoxide as a carbonyl source. Acyl azide glycals were used as synthetic intermediates in obtaining new acyl urea glycals via carbonylative coupling catalyzed by Pd(OAc)2 and 1,10‐Phen. Different glycal substrates, including disaccharide‐type, were studied, and various acyl azides and acyl ureas were prepared. Reaction yields were moderate to high (31–99 %) and reaction time varying from short to long (0.5–20 h).
- Subjects
AZIDATION; AZIDES; CARBONYLATION; GLYCOCONJUGATES; CARBON monoxide; CHEMICAL yield; GLYCALS
- Publication
European Journal of Organic Chemistry, 2020, Vol 2020, Issue 25, p3847
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202000494