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Metal-Free Syntheses of α-Ketothioamide and α-Ketoamide Derivatives from Sulfoxonium Ylides

Trayambek Nath Chaubey, Paran J. Borpatra, Ajay Sharma and Satyendra Kumar Pandey*

*Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi, Uttar Pradesh 221005, India, Email:

T. N. Chaubey, P. J. Borpatra, A. Sharma, S. K. Pandey, Org. Lett., 2022, 24, 8062-8066.

DOI: 10.1021/acs.orglett.2c03371

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The reaction of sulfoxonium ylides with primary or secondary amines afforded α-ketothioamides in the presence of elemental sulfur, whereas α-ketoamides were produced when I2 and TBHP were present. This simple, scalable reaction proceeded well at room temperature, tolerated a range of functional group, and generated the corresponding products in very good yields.

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proposed mechanism

Key Words

thioamides (thionation, amination), amides (oxidation, amination), multicomponent reactions, TBHP

ID: J54-Y2022