Issue 12, 2022

Electrochemical cascade synthesis of α-thio-substituted masked aldehydes

Abstract

The recent upsurge in electrosynthesis has provided efficient and sustainable synthetic strategies for procuring valuable molecules and their precursors. In this context, we have achieved an efficient cascade synthesis of β,β-dialkoxy sulfides under ambient electrochemical conditions. The electrolysis of terminal aryl alkynes, aromatic and aliphatic thiols, and alcohols initiates a cascade sequence involving the thiol–yne reaction/1,2-thio migration via nucleophilic attack of alkoxides to provide α-thio-substituted masked aldehydes in good yields for a diverse range of substrates. The cascade sequence also works well when using acetic acid and acetic anhydride instead of alcohols.

Graphical abstract: Electrochemical cascade synthesis of α-thio-substituted masked aldehydes

Supplementary files

Article information

Article type
Communication
Submitted
03 Mar 2022
Accepted
17 May 2022
First published
19 May 2022

Green Chem., 2022,24, 4783-4788

Electrochemical cascade synthesis of α-thio-substituted masked aldehydes

D. Sharma, Y. Hussain, M. Sharma and P. Chauhan, Green Chem., 2022, 24, 4783 DOI: 10.1039/D2GC00845A

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