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Tang, R.-Y., Science of Synthesis Knowledge Updates, (2024) 1, 336.
Potassium carbonate and a catalytic amount of N,N-diethylaniline can promote the sulfurization of amides with phosphorus pentasulfide. N,N-Diethylaniline may react with phosphorus pentasulfide to form an active thionating agent for sulfurization of amides. The sulfurization of aryl and alkyl amides 1 proceeds well in dichloromethane under reflux conditions, providing primary and secondary thioamides 2 in moderate to high yields (Scheme 2).[5] This method is also applicable to the transformation of esters into thioesters.
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Me | Me | 8 | 88 | [8] |
Me | Me | 8 | 88 | [8] |
8-MeMM8M8 | M | 8 | 88 | [8] |
8-e-MeM8M8 | M | 8 | 88 | [8] |
8-MeM8M8 | M | 8 | 88 | [8] |
8-Mee | M | 8 | 88 | [8] |
Me | Me | 8 | 88 | [8] |
e-Me | Me | eeeeeeeee | 88 | [8] |
Me | Me | 8 | >88 | [8] |
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References
[5] | Meee, M.-M.; Me, M.-M.; Meee, M.-M.; Me, M.-M., Meeeeeeeeee, (8888) 88, 888. |