Diastereoselective and Synergistic Gold‐Catalyzed Bispropargylation of Xanthones and Thioxanthones: An Access to Xanthene Derivatives

A gold‐catalyzed bispropargylation of xanthone derivatives is described. The use of propargylsilanes permits to achieve a deoxygenative bispropargylation through a double catalytic addition of the corresponding allenylgold intermediate to the synergistically activated carbonyl moiety. This methodolo...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2022-08, Vol.364 (15), p.2620-2628
Main Authors: Fernández, Sergio, Allegue, Darío, Santamaría, Javier, Ballesteros, Alfredo
Format: Article
Language:English
Subjects:
Activated carbon
Carbonyls
Cycloaddition
Deoxygenation
Ethers
Gold
Homogeneous catalysis
Reaction intermediates
Silanes
Stereoselectivity
Synthetic methods
Thioxanthenone
Xanthenes
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Summary:A gold‐catalyzed bispropargylation of xanthone derivatives is described. The use of propargylsilanes permits to achieve a deoxygenative bispropargylation through a double catalytic addition of the corresponding allenylgold intermediate to the synergistically activated carbonyl moiety. This methodology works in a diastereoselective manner either with xanthone or thioxanthone derivatives. Monopropargylated xanthydrol silyl ethers were isolated as reaction intermediates and these species could be transformed into symmetrical and non‐symmetrical bispropargylated xanthenes. The formation of non‐symmetrical bispropargylated xanthenes could also be achieved through an one‐pot procedure. Finally, other interesting structures, such as propargylxanthylidenes, propargylxanthenes and bispropargylated xanthenes replacing the silicon moiety, were accessible following different one‐pot synthetic methodologies. In addition, bispropargylated xanthenes could perform a carbonylative [2+2+1] formal cycloaddition.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202200526