Agent for the C-H Nitration and the Construction of Isoxazoline Ring

N-Nitrosuccinimide (1) is a stable solid and can be utilized in photoredox nitration reactions.¹⁾ When styrene is treated with 1 and Ru(bpy)₃(PF₆)₂ as a photocatalyst under the irradiation of LED light, the alkene moiety is selectively nitrated at terminal position. In addition, when water or an alcohol is added under the same conditions, nitroalcohols or alkoxy nitroethane derivatives are given, respectively. Furthermore, the palladium-free ipso-nitration of arylboronic acids proceeds under the photoredox condition.²⁾ As another example, the construction of isoxazoline ring can be raised through the multi-component reaction of 1, alkene or alkyne in acetone solvent. In this way, many applications of 1 are anticipated due to its variety of reactivity in addition to the nitration.

Related Products

N1193

N-Nitrosuccinimide

T3435

Tris(2,2'-bipyridine)ruthenium(II) Bis(hexafluorophosphate) (= Ru(bpy)₃(PF₆)₂)

References

• 1) Synthetic Diversity from a Versatile and Radical Nitrating Reagent
  • K. Zhang, B. Jelier, A. Passera, G. Jeschke, D. Katayev, Chem. Eur. J. 2019, 25, 12929.
• 2) N-Nitroheterocycles: Bench-Stable Organic Reagents for Catalytic Ipso-Nitration of Aryl- and Heteroarylboronic Acids
  • K. Zhang, A. Budinská, A. Passera, D. Katayev, Org. Lett. 2020, 22, 2714.

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