Synthetic Applications of Nitrenium Ions

Wardrop, Duncan J.; Bowen, Edward G.

doi:10.1002/9781118560907.ch10

Cited by 12 publications

(5 citation statements)

References 342 publications

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“…Deprotonation and oxidation of the urea provide a diazaoxyallylic cation 13 , analogous to what we have proposed for the oxidative diaza-(4 + 3) reaction of dienes . It is established that hydroxamate esters efficiently undergo oxidation to an N -acyl nitrenium ion using hypervalent iodide reagents . Nucleophilic addition of the indole 5 at the C-3 position to the diaza-oxyallylic cation 13 provides the zwitterionic intermediate 14 .…”

mentioning

confidence: 60%

Oxidative (3 + 2) Cycloaddition Reactions of Diaza-Oxyallyl Cationic Intermediates and Indoles for the Synthesis of Imidazoloindolines

2016

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An oxidative diaza-(3 + 2) cycloaddition reaction of simple urea derivatives with substituted indoles has been developed. This transformation provides rapid access to highly functionalized imidazoloindolines that are represented in bioactive compounds. The reported method is compatible with a wide variety of functional groups and directly provides unique heterocyclic scaffolds from indoles and a simple urea derivative.

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confidence: 60%

Oxidative (3 + 2) Cycloaddition Reactions of Diaza-Oxyallyl Cationic Intermediates and Indoles for the Synthesis of Imidazoloindolines

2016

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“…Mal and coworkers reported the N-arylation of sulfonanilides by implementing the HSAB (hard-soft-acid-base) principle. 11 Nitrenium ions [56][57][58][59] are soft, and carbenium ions 10,[60][61] are hard electrophiles in nature. Similarly, they considered thealkyl or -alkoxy substituted arenes as hard and extended πconjugated systems as soft nucleophiles.…”

Section: Hard-soft Acid-base (Hsab) Controlmentioning

confidence: 99%

Weak Interactions in Carbon-Hetero Atom Bond Forming Reactions

Bose¹,

Mal²

2021

Prayogik Rasayan

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Controlling various reactions by multiple weak interactions or soft forces has become an widespread topic under supramolecular catalysis. This review has made a literature collection that explores cooperative weak or noncovalent interactions. These are charge transfer complexation, H-bonding, S-H…π, acid-base, cation- π, etc., towards C-hetero bond formation reactions. This review article will discuss the specific reactivity of chemical systems controlled by weak interactions.

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“…Divalent nitrogen species with six electrons in its valence shell containing a positive charge on nitrogen is recognized as nitrenium ion. − They are nitrogen analogues of carbenium ions which act as electrophiles for aromatic electrophilic substitution reactions. , Nitrenium ions have been known in the literature for a long time; , however, their use in organic synthesis is relatively less explored. − Nitrenium ions can be derived from amines (or amides) in hypervalent iodine(III)-mediated organic transformations . Electrochemical anodic oxidation techniques have also been used to generate nitrenium ions using iodine(III) reagent for preparation of valuable structural compounds. − Recently, we have developed sustainable methods for C–N bond synthesis by using iodine(III) reagents via nitrenium ions. − Mechanistically, generation of nitrenium ions includes two steps: ligand exchange of iodine(III) with amines and reductive elimination of iodoarene (Figure a).…”

Section: Introductionmentioning

confidence: 99%

Iodine(III)-Enabled Distal C–H Functionalization of Biarylsulfonanilides

2018

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Here we report a metal-free C-N coupling reaction for carbazole synthesis by distal (- meta) C-H bond functionalization. Nitrenium ion, a potential synthetic intermediate, was generated in situ from reactions of iodine(III) reagents and biarylsulfonanilides. Following, nitrenium ions were used for intramolecular dehydrogenative C-N coupling reactions via 1,2-alkyl (methyl or ethyl) migration by the expense of C-H bond functionalization at the distal position toward synthesis of 1,2,4-trialkyl-substituted carbazoles. The iodine(III) condition was either maintained by using a stoichiometric amount of phenyliodine diacetate (PIDA) or in-situ generated from iodobenzene (PhI)- meta-chloroperbenzoic acid ( mCPBA) combination.

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Synthetic Applications of Nitrenium Ions

Cited by 12 publications

References 342 publications

Oxidative (3 + 2) Cycloaddition Reactions of Diaza-Oxyallyl Cationic Intermediates and Indoles for the Synthesis of Imidazoloindolines

Oxidative (3 + 2) Cycloaddition Reactions of Diaza-Oxyallyl Cationic Intermediates and Indoles for the Synthesis of Imidazoloindolines

Weak Interactions in Carbon-Hetero Atom Bond Forming Reactions

Iodine(III)-Enabled Distal C–H Functionalization of Biarylsulfonanilides

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