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DOI: 10.1055/a-2601-4481
Magnetite-Catalyzed Cross-Dehydrogenative Coupling of Aldehydes and Thiols Forming Thioesters
Magnetite: A Green, Sustainable and Recyclable Catalyst for Direct Synthesis of Thioesters by C–H Activation.
Eur. J. Org. Chem. 2025;
28: e202400827
DOI: 10.1002/ejoc.202400827
Keywords
magnetite catalysis - cross dehydrogenative coupling - thioesterification - aldehydes - thiols
Significance
Magnetite (Fe3O4) promoted the cross-dehydrogenative coupling of aryl aldehydes 1 and thiols 2 in the presence of t BuOOH as a stoichiometric oxidant. The reactions were carried out under air at 70 °C for 1 hour with/without additional water (conditions A/B) to give the corresponding thioesters 3 (34 examples) in up to 96 % yield (eq 1). In the reaction of benzaldehyde (1a) and octadecane-1-thiol (2a), the catalyst was magnetically recovered and reused six times with only a gradual loss of its catalytic activity (fresh: 94 % yield, 7th run: 78 % yield).
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Comment
The reactions of aryl thiols proceeded efficiently without additional water (conditions B). Thus, S-phenyl benzothioate (3r) was obtained in 82 % yield under conditions B (13 % under conditions A). An aliphatic aldehyde, dodecanal (1 m), also underwent the cross-dehydrogenative coupling under similar conditions (2 examples) to afford 3 m and 3aj in 80 % and 49 % yields, respectively.
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Publication History
Article published online:
23 June 2025
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