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 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.
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thiocarbonylation;  selenocarbonylation;  C2-branched sugars;  glycals;  molybdenum hexacarbonyl

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Darbem MP., Esteves HA., Oliveira IM., Pimenta DC, Stefani HA.. Palladium-catalyzed thio- and selenocarbonylation of 2-iodoglycals. ChemCatChem. 2020 Jan;12:576-583. doi:10.1002/cctc.201901403.
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