Permethylated Salts and Radicals Derived from Azo <i>peri‐</i>Naphthalenes

Bohle, D. Scott; Chua, Zhijie; Johnstone, Timothy C.; Moiseev, Andrey G.; Perepichka, Inna; Rosadiuk, Kristopher A.

doi:10.1002/cplu.201200021

Cited by 9 publications

(7 citation statements)

References 41 publications

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“…In line with literature reports, compound 1 was prepared in moderate yield, by oxidation of diaminonapthalene and subsequent methylation . Noted in both this report by Bohle et al.…”

Section: Figuresupporting

confidence: 85%

Nitrenium Salts in Lewis Acid Catalysis

Mehta

Goicoechea

2020

Angewandte Chemie

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Molecular compounds featuring nitrogen atoms are typically regarded as Lewis bases and are extensively employed as donor ligands in coordination chemistry or as nucleophiles in organic chemistry. By contrast, electrophilic nitrogen‐containing compounds are much rarer. Nitrenium cations are a new family of nitrogen‐based Lewis acids, the reactivity of which remains largely unexplored. In this work, nitrenium ions are explored as catalysts in five organic transformations. These reactions are the first examples of Lewis acid catalysis employing nitrogen as the site of substrate activation. Moreover, these compounds are readily accessed from commercially available reagents and exhibit remarkable stability toward moisture, allowing for benchtop transformations without the need to pretreat solvents.

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“…In line with literature reports, compound 1 was prepared in moderate yield, by oxidation of diaminonapthalene and subsequent methylation . Noted in both this report by Bohle et al.…”

Section: Figuresupporting

confidence: 85%

Nitrenium Salts in Lewis Acid Catalysis

Mehta

Goicoechea

2020

Angewandte Chemie

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“…In line with literature reports,c ompound 1 was prepared in moderate yield, by oxidation of diaminonapthalene and subsequent methylation. [48] Noted in both this report by Bohle et al and the crystallographic data acquired by us,aweak interaction between the Lewis acidic nitrogen centre and the trifluoromethanesufonate anion could be observed.…”

Section: Nitrenium Salts In Lewis Acid Catalysissupporting

confidence: 54%

Nitrenium Salts in Lewis Acid Catalysis

Mehta

Goicoechea

2020

Angew Chem Int Ed

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Molecular compounds featuring nitrogen atoms are typically regarded as Lewis bases and are extensively employed as donor ligands in coordination chemistry or as nucleophiles in organic chemistry.B yc ontrast, electrophilic nitrogencontaining compounds are muchr arer.N itrenium cations are an ew family of nitrogen-based Lewis acids,t he reactivity of which remains largely unexplored. In this work, nitrenium ions are explored as catalysts in five organic transformations.These reactions are the first examples of Lewis acid catalysis employing nitrogen as the site of substrate activation. Moreover,these compounds are readily accessed from commercially available reagents and exhibit remarkable stability toward moisture,a llowing for benchtop transformations without the need to pretreat solvents.

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“…Indeed, when compound 2a was irradiated with UV-light, the signal of the corresponding radical 4a was observed by electron paramagnetic resonance (EPR) (Scheme ). Although such a radical has never been isolated before, its lifetime was estimated to be roughly a few minutes . Nonetheless, when 4a is obtained photochemically from 2a , the half-life proved to be ca.…”

Section: Resultsmentioning

confidence: 97%

Multimodal Reactivity of N–H Bonds in Triazanes and Isolation of a Triazinyl Radical

et al. 2022

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The employment of nitrogen Lewis acids based on nitrenium cations has been increasingly featured in the fields of main group chemistry and catalysis. A formally reduced form of nitrenium D�cyclic triazanes E�are intriguing chemical compounds, the chemistry of which is completely unexplored. In this work, we reveal that N−H-triazanes exhibit unusual N−H bond properties; namely, they can serve as protons, hydrides, or hydrogen atom donors. This unique multimodal reactivity provides an N-cation, N-anion, or N-radical from the same species. It allowed us to isolate, for the first time, a stable naphto[1,2,3]triazinyl radical, which was fully characterized both computationally and experimentally, including its monomeric X-ray structure. Moreover, this radical can be prepared directly from the nitrenium cation by a single electron reduction (E = −0.46 V), and this process is reversible. We envision versatile uses of this radical in synthetic and materials chemistry.

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Permethylated Salts and Radicals Derived from Azo peri‐Naphthalenes

Cited by 9 publications

References 41 publications

Nitrenium Salts in Lewis Acid Catalysis

Nitrenium Salts in Lewis Acid Catalysis

Nitrenium Salts in Lewis Acid Catalysis

Multimodal Reactivity of N–H Bonds in Triazanes and Isolation of a Triazinyl Radical

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