Palladium‐Catalyzed Thio‐ and Selenocarbonylation of 2‐Iodoglycals

The carbonylative cross‐coupling reactions of 2‐iodoglycals with thiols and selenols in the presence of molybdenum hexacarbonyl as a solid source of carbon monoxide is described. This methodology permitted the synthesis of 29 C2‐glycosides bearing thioester and selenoester functionalities in moderat...

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Bibliographic Details
Published in:ChemCatChem 2020-01, Vol.12 (2), p.576-583
Main Authors: Darbem, Mariana P., Esteves, Henrique A., Oliveira, Isadora M., Pimenta, Daniel C., Stefani, Hélio A.
Format: Article
Language:English
Subjects:
C2-branched sugars
Carbon monoxide
Carbonyls
Chemical reactions
Cross coupling
Functional groups
glycals
molybdenum hexacarbonyl
Palladium
selenocarbonylation
thiocarbonylation
Thiols
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Summary:The carbonylative cross‐coupling reactions of 2‐iodoglycals with thiols and selenols in the presence of molybdenum hexacarbonyl as a solid source of carbon monoxide is described. This methodology permitted the synthesis of 29 C2‐glycosides bearing thioester and selenoester functionalities in moderate to excellent yields and high functional group tolerance. Moreover, this communication describes the first catalytic carbonylative coupling reaction of selenols with a carbon electrophile. Are you in a rush? Carbonylative cross‐coupling reactions of 2‐iodoglycals with thiols (RSH) and selenols (RSeH) in the presence of molybdenum hexacarbonyl as a solid source of carbon monoxide is described. A useful methodology for the synthesis of chalcogen‐containing C2‐glycosides with high functional group tolerance.
ISSN:1867-3880
1867-3899
DOI:10.1002/cctc.201901403