Hydroxyamine Derivative for the Amination of Alkenes and Thiols

O-Pivaloylhydroxyammonium triflate (1) is reported as an aminating reagent with a unique reactivity. For instance, 1 can regioselectively introduce amino and hydroxy/alkoxy groups to styrene derivatives in high yields by using the iron complex as a catalyst in water or alcohol solvent.¹⁾ In addition, unprotected sulfinamides are obtained in the single-step reaction of thiols and 1 in alcohol solvent.²⁾

References

• 1) Direct Catalytic Synthesis of Unprotected 2-Amino-1-Phenylethanols from Alkenes by Using Iron(II) Phthalocyanine
• L. Legnani, B. Morandi, Angew. Chem. Int. Ed. 2016, 55, 2248.
• 2) Hydroxylamine-Derived Reagent as a Dual Oxidant and Amino Group Donor for the Iron-Catalyzed Preparation of Unprotected Sulfinamides from Thiols
• S. Chatterjee, S. Makai, B. Morandi, Angew. Chem. Int. Ed. 2021, 60, 758.

Related Compounds

P0774

Iron(II) Phthalocyanine (= Fe^IIPC)

B0468

2,2'-Bipyridyl (= bpy)

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