Palladium‐Catalyzed/Mn(OAc) 3 ‐Mediated 1,2‐Diazidation and 1,2‐Acetoxy/Hydroxylation of N ‐Allyl Sulfonamides - Sorbonne Université Access content directly
Journal Articles (Review Article) Advanced Synthesis and Catalysis Year : 2024

Palladium‐Catalyzed/Mn(OAc) 3 ‐Mediated 1,2‐Diazidation and 1,2‐Acetoxy/Hydroxylation of N ‐Allyl Sulfonamides

Marta Papis
  • Function : Author
Sara Colombo
  • Function : Author
Leonardo Lo Presti
  • Function : Author
Giovanni Poli
Gianluigi Broggini
  • Function : Author
Camilla Loro

Abstract

Palladium‐catalyzed conditions for diazidation or acetoxy/hydroxylation of N ‐allyl sulfonamides by using Pd(OAc) 2 as the catalyst combined with Mn(OAc) 3 ⋅ 2H 2 O have been developed. The 1,2‐diazidation reaction of the carbon‐carbon double bond occurs in mild conditions ( i. e . NaN 3 as azide source in THF at room temperature), whereas the 1,2‐acetoxy/hydroxylation requires an excess of Mn(OAc) 3 ⋅ 2H 2 O. The well‐known ability of this reagent to act through single‐electron transfer (SET) makes plausible a radical mechanism involving high valent palladium complexes.
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Dates and versions

hal-04576557 , version 1 (15-05-2024)

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Marta Papis, Sara Colombo, Leonardo Lo Presti, Giovanni Poli, Gianluigi Broggini, et al.. Palladium‐Catalyzed/Mn(OAc) 3 ‐Mediated 1,2‐Diazidation and 1,2‐Acetoxy/Hydroxylation of N ‐Allyl Sulfonamides. Advanced Synthesis and Catalysis, 2024, ⟨10.1002/adsc.202400035⟩. ⟨hal-04576557⟩
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