One-Pot Synthesis of Sulfilimines from Sulfenamides Using Aldehydes as an Alkyl Source

Herein, we present a direct and efficient one-pot synthesis of sulfilimines starting from sulfenamides and aldehydes as an alkyl source. The reaction sequence comprises the in situ transformation of aldehyde into alkyl iodide via an alcohol intermediate. Iodide subsequently reacts with sulfenamide in the same pot to furnish the desired sulfilimines. Notably, alcohols can also be used directly in this protocol to access the same sulfilimines. To the best of our knowledge, this is the first report utilizing aldehydes as coupling partners for sulfilimine preparation. The use of readily available, inexpensive aldehydes (as an alkylating agent), operational simplicity, and gram-scale compatibility are the advantages of the protocol. Sulfilimine derivatives of levetiracetam (antiepileptic drug) are successfully synthesized. Additionally, the obtained sulfilimine is further transformed to sulfoximine, demonstrating the synthetic utility of the product.