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Sulfonylimino Group Transfer Reaction Using Imino-?³-iodanes with I? as Catalyst Under Metal-free Conditions.

ABSTRACT: A new practical procedure of imination for sulfide has been developed. The treatment of (N-tosylimino)-phenyl-?³-iodane, PhINTs, with various sulfides in the presence of a catalytic amount of I? 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-?³-iodane to sulfide under the conditions may involve radical steps within the reaction mechanism.

SUBMITTER: Yoshimura A

PROVIDER: S-EPMC6429398 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature

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Sulfonylimino Group Transfer Reaction Using Imino-λ³-iodanes with I₂ as Catalyst Under Metal-free Conditions.

Yoshimura Akira A Makitalo Cody L CL Jarvi Melissa E ME Shea Michael T MT Postnikov Pavel S PS Rohde Gregory T GT Zhdankin Viktor V VV Saito Akio A Yusubov Mekhman S MS

Molecules (Basel, Switzerland) 20190311 5

A new practical procedure of imination for sulfide has been developed. The treatment of (<i>N</i>-tosylimino)-phenyl-λ³-iodane, PhINTs, with various sulfides in the presence of a catalytic amount of I₂ under metal-free conditions affords the corresponding <i>N</i>-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 ...[more]

PMID: 30862025

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