[N-(Methylsulfonyl)imino]phenyliodinane

CAS 181306-49-0, Cat. No EN300-52982576
Reagent for N-transfer

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[N-(Methylsulfonyl)imino]phenyliodinane (PhI=NMs) is a stable, hypervalent iodine(III) reagent used for nitrene (–NMs) transfer. It is more soluble than aryl-substituted analogs¹ (EN300-20000353) and reacts efficiently under mild conditions. In sulfoximine synthesis², it reacts with various sulfoxides (alkyl–aryl, dialkyl, vinyl, allylic, acetylenic) under copper(II) triflate catalysis in acetonitrile, providing high yields (40–98%) with full retention of stereochemistry at sulfur, including for chiral sulfoxides. In aminofluorination of styrenes³, PhI=NMs enables copper-catalyzed regioselective formation of β-fluoro-N-mesylphenethylamines. The reaction tolerates a broad range of substituted styrenes, including para/meta methyl, halogen, OAc, and internal alkenes, with high yields. However, unactivated alkenes lead to aziridines formation. Overall, this reagent is versatile and selective for nitrene transfer in both sulfur imidation and alkene functionalization.

Synonyms: N-(phenyl-lambda3-iodanylidene)methanesulfonamide; N-(phenyl-3-iodanylidene)methanesulfonamide; methansulfonimidophenyliodonium-ylid; iodonium, [(methylsulfonyl)amino]phenyl-, inner salt