CAS 5336-95-8, Cat. No EN300-3476413
Reagent for nitration
N-Nitro-succinimide is a nitrating reagent derived from succinimide, capable of C-H bond diversification of alkenes and alkynes to create β-nitroalkenes, β-nitrohydrins, and β-nitroethers1. The reagent reacts under mild conditions utilizing a nitryl radical mechanism facilitated by photoredox catalysis. The approach offers chemoselective nitration without over-nitration issues and is particularly effective for late-stage functionalization in organic synthesis. There exists an effective protocol for aromatic substrates as well2. The reagent is easy to handle, bench-stable, and provides persistent good yields.
Synonyms: 1-nitropyrrolidine-2,5-dione; 1-nitro-2,5-pyrrolidinedione; 1-nitro-2,5-pyrrolidine-dione; N-nitrosuccinimide
Selected publications
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Synthetic Diversity from a Versatile and Radical Nitrating Reagent.
Zhang K.; Jelier B.; Passera A.; Jeschke G.; Katayev D. Chemistry - A European Journal 2019, 25 (56), 12929–12939. DOI: 10.1002/chem.201902966
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N-Nitroheterocycles: Bench-Stable Organic Reagents for Catalytic Ipso-Nitration of Aryl- And Heteroarylboronic Acids.
Zhang K.; Budinská A.; Passera A.; Katayev D. Org Lett 2020, 22 (7), 2714–2719. DOI: 10.1021/acs.orglett.0c00671