Blue LED‐Promoted Oxathiacetalization of Aldehydes and Ketones

In synthetic chemistry, the protection of aldehydes and ketones is crucial during multistep synthesis of complex molecules. Organic chemists have paid substantial attention to the synthesis of 1,3‐oxathiolanes and 1,3‐oxathianes because of their considerable stability under acidic conditions and eas...

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Bibliographic Details
Published in:European journal of organic chemistry 2020-05, Vol.2020 (17), p.2542-2552
Main Authors: Liu, You‐Chen, Reddy, Daggula Mallikarjuna, Chen, Xin‐An, Shieh, Yi‐Chen, Lee, Chin‐Fa
Format: Article
Language:English
Subjects:
Aldehydes
Ambient temperature
Chemical synthesis
Chemists
Ketones
Light emitting diodes
Mercaptoalcohol
Oxathiacetalization
Photoredox catalysis
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Summary:In synthetic chemistry, the protection of aldehydes and ketones is crucial during multistep synthesis of complex molecules. Organic chemists have paid substantial attention to the synthesis of 1,3‐oxathiolanes and 1,3‐oxathianes because of their considerable stability under acidic conditions and ease of removal of protecting groups. In this paper, we report the mild and efficient oxathiacetalization of aldehydes with 2‐mercaptoethanol and 3‐mercaptopropan‐1‐ol through visible‐light‐promoted eosin‐Y catalyzed C–S and C–O bond formation at ambient temperature under metal‐free conditions. This catalytic system also affords oxathiacetalization of ketones through photoredox catalysis. A visible‐light‐promoted oxathiacetalization of aldehydes and ketones with 2‐mercaptoethanol and 3‐mercaptopropan‐1‐ol in the presence of eosin Y as catalyst is described leading to the formation of 1,3‐oxathiolanes and 1,3‐oxathianes at ambient temperature and under metal‐free conditions. The solvent is playing vital role in the protection of carbonyl compounds with mercaptoalcohol.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202000218