CO‐Boosted Protocol for the Photocatalytic C−H Thiolation of Aldehydes Using Phenylthiobenzenesulfonate

The formyl C−H thiolation of aldehydes using thiosulfonates and the decatungstate anion as a photocatalyst is reported. Using this photocatalytic protocol together with a CO atmosphere, both aromatic and aliphatic thioesters can be synthesized in good yields. The transformation consists of a cascade...

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Bibliographic Details
Published in:European journal of organic chemistry 2024-07, Vol.27 (28), p.n/a
Main Authors: Pan, Lin‐Wei, Taniguchi, Nobukazu, Hyodo, Mamoru, Ryu, Ilhyong
Format: Article
Language:English
Subjects:
acyl radical
Aldehydes
carbon monoxide
Cascade chemical reactions
Chemical synthesis
Photocatalysis
SH2 reaction
thioester
thiosulfonate
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Summary:The formyl C−H thiolation of aldehydes using thiosulfonates and the decatungstate anion as a photocatalyst is reported. Using this photocatalytic protocol together with a CO atmosphere, both aromatic and aliphatic thioesters can be synthesized in good yields. The transformation consists of a cascade of double SH2 reactions, HAT and an ArS group transfer. CO atmosphere effectively limits the extent of decarbonylation of acyl radicals that are generated in the reaction. The formyl C−H thiolation of aldehydes using phenylthio benzenesulfonate was achieved using a decatungstate anion as a photocatalyst under CO atmosphere, giving good yields of thioesters.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202400138