Vinyl- and Arylnitrogen Compounds

Chiara, José Luis

doi:10.1016/b0-08-044655-8/00037-4

Cited by 9 publications

(7 citation statements)

References 896 publications

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“…Unfortunately, nitrated products were not obtained from toluene, N , N -dimethylaniline, thioanisole, and chlorobenzene even at 130 °C. Nitroarenes are useful building blocks in organic synthesis and are also constituents for dyes, rubber, plastics, and pharmaceuticals . Their synthetic potential as coupling partners in Suzuki–Miyaura cross-coupling and Buchwald–Hartwig amination was also recently reported .…”

Section: Resultsmentioning

confidence: 97%

“…Because of the low LUMO energy level of 9-silafluorene derivatives originating from conjugation between the exocyclic Si–C σ* orbital and the π* orbital of the biaryl backbone, these compounds have attracted attention as promising components of novel advanced functional materials, such as light-emitting diodes, field-effect transistors, photovoltaic cells, and fluorescent probes (Figure ). , Thus, the development of simple and efficient chemical modification methods could provide compounds with new electro- and physical properties and could further extend the utility of 9-silafluorene derivatives as new functional molecules. Most previous modification methods introduced functional groups before construction of the 9-silafluorene framework. , A frequently employed method has been the reaction of organolithium or magnesium reagents derived from functionalized 2,2′-dihalobiaryls with dichlorosilanes.…”

Section: Introductionmentioning

confidence: 99%

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Regioselective Functionalization of 9,9-Dimethyl-9-silafluorenes by Borylation, Bromination, and Nitration

et al. 2019

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Despite the utility of 9-silafluorenes as functional materials and as building blocks, methods for efficient functionalization of their backbone are rare, probably because of the presence of easily cleavable C–Si bonds. Although controlling the regioselectivity of iridium-catalyzed direct borylation of C–H bonds is difficult, we found that bromination and nitration of 2-methoxy-9-silafluorene under mild conditions occurred predominantly at the electron-rich position. The resulting product having methoxy and bromo groups can be utilized as a building block for the synthesis of unsymmetrically substituted 9-silafluorene-containing π-conjugated molecules.

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Section: Resultsmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

Regioselective Functionalization of 9,9-Dimethyl-9-silafluorenes by Borylation, Bromination, and Nitration

et al. 2019

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“…Then, a further improvement on the overall process could be the use of aniline as starting reagent. In fact, the production of the cyclohexanone oxime, integrated with a process of benzene amination may represent a step forward in the sense of a more sustainable process [17,18].…”

Section: Introductionmentioning

confidence: 99%

A New Sustainable Multistep Catalytic Process from Benzene to Caprolactam: Amination, Hydroximation and Beckmann Rearrangement Promoted and Catalyzed by Trifluoroacetic Acid

et al. 2022

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Here we report some results on a 3 steps benzene caprolactam process via amination, aniline Hydroxymation and Beckmann rearrangement. The amination proceeds with hydroxylamine trifluoroacetate, with 97% of conversion and selectivity of 90%, catalyzed by V compounds. We achieve 98% of conversion and 95% of selectivity in the hydroxymation of aniline in the presence of hydroxylamine trifluoroacetate, sulfonic resin and Pd/C. While in the absence of the resin, hydrogenation of hydroxylamine trifluoroacetate occurs readily to the ammonium salt. The reaction occurs likely by the exchanged hydroxylamine and the aniline reduction intermediate. The use of hydroxylamine trifluoroacetate, instead of the chloride, favors the sustainability of the process by avoiding the ammonium chloride formation. The absence of salt except those derived from the trifluoroacetic acid allows a complete reuse of the trifluoroacetic acid and the only byproduct is ammonium nitrate obtained by resin regeneration. Beckmann rearrangement of the so produced cyclohexanone oxime occurs easily after diethyl ether evaporation and additions of a solution trifluoroacetic acid acetonitrile in high yield and selectivity.

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“…There have been a number of short reviews pertinent to this work that have appeared over the last 15 years or so, and these have highlighted various aspects of sulfamic acid and sulfamide chemistry. An important encyclopedia on reagents for organic synthesis , has useful entries on both as has a compendium on organic functional group transformations . A 2007 chemical technology encyclopedia has a substantial number of short entries on sulfamic acid, sulfamates, sulfamoyl halides, sulfonation, sulfation, and sulfur compounds…”

Section: Introductionmentioning

confidence: 99%