Journal
MOLECULES
Volume 24, Issue 5, Pages -Publisher
MDPI
DOI: 10.3390/molecules24050979
Keywords
iminoiodanes; imination; sulfide; sulfilimine; phosphine; iminophosphorane; amidyl radical; catalytic cycle; iodine
Funding
- Russian Science Foundation [RSF-16-13-10081, RSF-19-13-00011]
- Tomsk Polytechnic University Competitiveness Enhancement Program
- JSPS Fund for the Promotion of Joint International Research [16KK0199]
- Grants-in-Aid for Scientific Research [16KK0199] Funding Source: KAKEN
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A new practical procedure of imination for sulfide has been developed. The treatment of (N-tosylimino)-phenyl-lambda(3)-iodane, PhINTs, with various sulfides in the presence of a catalytic amount of I-2 under metal-free conditions affords the corresponding N-tosylsulfilimine compounds with moderate to good yields. This facile transfer procedure of the sulfonylimino group can also be applied to triphenylphosphine to produce the respective iminotriphenylphosphoranes in high yields. According to the reaction mechanism studies, the process of imination from (N-tosylimino)-phenyl-lambda(3)-iodane to sulfide under the conditions may involve radical steps within the reaction mechanism.
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