Chemistry of Peri‐condensed pyrroles. Synthesis of 4H‐naphtho[1,4‐def]carbazole. A new route to nitrotriphenylenes

Klemm, L. H.; Hall, E.; Sur, Sandip K.

doi:10.1002/jhet.5570250531

Cited by 13 publications

(3 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Otherwise, it can serve as a nitro-methylating agent in cross-coupling reactions , and conjugate additions under basic conditions. − Surprisingly, we observed that the combination of PIFA with a NaX can facilitate nitration instead of cross-coupling (see Scheme S1 in the Supporting Information). To the best of our knowledge, there have been no reports of nitrations with CH 3 NO 2 , which encouraged us to develop CH 3 NO 2 as an organo-nitrating reagent.…”

mentioning

confidence: 99%

PIFA-Promoted, Solvent-Controlled Selective Functionalization of C(sp²)–H or C(sp³)–H: Nitration via C–N Bond Cleavage of CH₃NO₂, Cyanation, or Oxygenation in Water

2019

View full text Add to dashboard Cite

A novel nitration (via C(sp 3 )−N breaking/ C(sp 2 )−N formation with CH 3 NO 2 ) mediated by [bis-(trifluoroacetoxy)iodo]benzene (PIFA) is described. The NO 2 transfer from CH 3 NO 2 to the aromatic group of the substrate is possible with careful selection of the solvent, NaX, and oxidant. In addition, the solvent-controlled C(sp 2 )−H functionalization can shift to an α-C(sp 3 )−H functionalization (cyanation or oxygenation) of the α-C(sp 3 )−H of cyclic amines.

show abstract

mentioning

confidence: 99%

PIFA-Promoted, Solvent-Controlled Selective Functionalization of C(sp²)–H or C(sp³)–H: Nitration via C–N Bond Cleavage of CH₃NO₂, Cyanation, or Oxygenation in Water

2019

View full text Add to dashboard Cite

show abstract

“…In the traditional synthetic method, treatment of carbazole with acetic acid or acetamide and anhydrous phosphorus pentoxide or zinc chloride at 150 C provided 4H-benzo[def]carbazole (Scheme 1a) [21]. Besides, calcium oxide was used to react with aminophenanthrene at high temperature which promoted intramolecular cyclization and generated 4H-benzo[def]carbazole (Scheme 1b) [22][23][24][25].…”

Section: S C H E M Ementioning

confidence: 99%

Synthesis and photophysical properties of fluorescent 8,9‐diarylbenzo[def]carbazoles

Hsiao

Liang

Chen

et al. 2023

J Chinese Chemical Soc

View full text Add to dashboard Cite

Background Benzocarbazole has attracted much attention from scientists in the past few decades for a variety of applications in materials science. Objective Herein we report the synthesis and photophysical properties of N‐acyl and N‐free 8,9‐diarylbenzo[def]carbazoles. Methods These benzo[def]carbazoles were prepared by Pd(II)‐catalyzed C‐H bond activation and deacetylation as the key steps, and their photophysical properties were studied by measurement of absorption and emission spectra in chloroform at room temperature. Results The 8,9‐diarylbenzo[def]carbazoles show lower LUMO energy levels and smaller HOMO/LUMO gap compared to the parent benzo[def]carbazole, and the N‐unprotected 8,9‐diarylbenzo[def]carbazoles show more red‐shifted fluorescent emission compared to the N‐acyl ones. The absorption and emissionmaxima of these 8,9‐diaryl‐substituted benzo[def]carbazoles in CHCl3 were in the ranges of 278–350 and 365–426 nm, respectively, and with quantum yields (ΦF) up to 0.62. Conclusions We have demonstrated the photophysical properties of 8,9‐diaryl substituted benzo[def]carbazoles with or without N‐acetyl group. These 8,9‐diaryl substituted benzo[def]carbazoles could be good candidates for the future development of functional organic molecules.

show abstract

“…77 The first reported example of the use of nitromethane as a nitrating reagent was shown by Klemm and co-workers in 1988 during the sulfonylation of polyaromatics. 78 However, this transformation used nitromethane that had been stored in a bottle for 20 years and this makes it is difficult to determine if the nitromethane was the real source of NO 2 .…”

Section: Nitroalkanesmentioning

confidence: 99%

Organic Nitrating Reagents

Patra¹,

Mosiagin²,

Katayev³

et al. 2022

Synthesis

View full text Add to dashboard Cite

Nitro compounds are vital raw chemicals that are widely used in academic laboratories and industries for the preparation of various drugs, agrochemicals, and materials. Thus, nitrating reactions are of great importance for chemists and are even taught in schools as one of the fundamental transformations in organic synthesis. Since the discovery of the first nitrating reactions in the 19th century, progress in this field has been constant. Yet, for many years the classical electrophilic nitration approach using a mixture of strong mineral acids dominated the field. However, in recent decades, the attention of researchers has focused on new reactivity and new reagents that can provide access to nitro compounds in a practical and straightforward way under mild reaction conditions. Organic nitrating reagents have played a special role in this field since they have enhanced reactivity. They also allow nitration to be carried out in an ecofriendly and sustainable manner. This review examines the development and application of organic nitrating reagents.1 Introduction2 Organic Nitrating Reagents2.1 Alkyl Nitrites2.2 Nitroalkanes2.3 Alkyl Nitrates2.4 N-Nitroamides2.5 N-Nitropyrazole2.6 N-Nitropyridinium Salts3 Organic Nitrating Reagents Generated In Situ3.1 Acyl Nitrates3.2 Trimethylsilyl Nitrate3.3 Nitro Onium Salts4 Organic Nitronium Salts5 Organic Nitrates and Nitrites5.1 Ammonium Nitrates5.2 Heteroarylium Nitrates5.3 Other Organic Nitrates5.4 Organic Nitrites6 Conclusion and Outlook

show abstract

Chemistry of Peri‐condensed pyrroles. Synthesis of 4H‐naphtho[1,4‐def]carbazole. A new route to nitrotriphenylenes

Cited by 13 publications

References 23 publications

PIFA-Promoted, Solvent-Controlled Selective Functionalization of C(sp²)–H or C(sp³)–H: Nitration via C–N Bond Cleavage of CH₃NO₂, Cyanation, or Oxygenation in Water

PIFA-Promoted, Solvent-Controlled Selective Functionalization of C(sp²)–H or C(sp³)–H: Nitration via C–N Bond Cleavage of CH₃NO₂, Cyanation, or Oxygenation in Water

Synthesis and photophysical properties of fluorescent 8,9‐diarylbenzo[def]carbazoles

Organic Nitrating Reagents

Contact Info

Product

Resources

About

Chemistry of Peri‐condensed pyrroles. Synthesis of 4H‐naphtho[1,4‐def]carbazole. A new route to nitrotriphenylenes

Cited by 13 publications

References 23 publications

PIFA-Promoted, Solvent-Controlled Selective Functionalization of C(sp2)–H or C(sp3)–H: Nitration via C–N Bond Cleavage of CH3NO2, Cyanation, or Oxygenation in Water

PIFA-Promoted, Solvent-Controlled Selective Functionalization of C(sp2)–H or C(sp3)–H: Nitration via C–N Bond Cleavage of CH3NO2, Cyanation, or Oxygenation in Water

Synthesis and photophysical properties of fluorescent 8,9‐diarylbenzo[def]carbazoles

Organic Nitrating Reagents

Contact Info

Product

Resources

About

PIFA-Promoted, Solvent-Controlled Selective Functionalization of C(sp²)–H or C(sp³)–H: Nitration via C–N Bond Cleavage of CH₃NO₂, Cyanation, or Oxygenation in Water

PIFA-Promoted, Solvent-Controlled Selective Functionalization of C(sp²)–H or C(sp³)–H: Nitration via C–N Bond Cleavage of CH₃NO₂, Cyanation, or Oxygenation in Water