Facile synthetic protocols for perfluoroalkyl-substituted diazapentaphenes

Yamada, Shigeyuki; Iwama, Shota; Kinoshita, Keiji; Yamazaki, Takashi; Kubota, Toshio; Yajima, Tomoko

doi:10.1016/j.tet.2014.07.069

Cited by 14 publications

(10 citation statements)

References 26 publications

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“…The cyclisation substrate 225 was prepared by benzyne insertion into para ‐phenylenediamine‐bis(trifluoroacetamide) 224 . Double ring closure to 226 was secured with hot trifluoroacetic acid . An exactly comparable double ring closure but with methyl instead of trifluoromethyl, was brought about with catalytic sulfuric acid in refluxing acetic acid .…”

Section: Pyrido[32‐a]acridine {Benzo[b][47]phenanthroline}mentioning

confidence: 99%

“…[139] acetic acid. [140] An exactly comparable double ring closure but with methyl instead of trifluoromethyl, was brought about with catalytic sulfuric acid in refluxing acetic acid. [121] Product 226 can also be accessed via reaction of ortho-aminophenyl trifluoromethyl ketone with cyclohexane-1,4-dione giving 227, easily dehydrogenated (Scheme 78).…”

Section: Pyrido[32-a]acridine {Benzo[b][47]phenanthroline}mentioning

confidence: 99%

“…[140,141] The condensing cyclisations of N,N′-diphenyl-para-phenylenediamine 228 with carboxylic acids or dicarboxylic acids, produces helical species, by virtue of the steric interference between the R 1 groups or constraint from the introduced ring; structures 229 and 230 are examples (Scheme 79). [140,141] Scheme 79. Syntheses of helical dibenzo[b,j] [4,7]phenanthrolines 229 and 230.…”

Section: Pyrido[32-a]acridine {Benzo[b][47]phenanthroline}mentioning

confidence: 99%

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Pyridoacridines in the 21st Century

Joule

Álvarez

2019

Eur J Org Chem

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This minireview summarizes the work developed during this century with compounds containing the pyridoacridine scaffold in its different isomeric forms. The isolation of natural products, syntheses, bioactivities, chelation capacity, and other properties of compounds containing this framework are discussed. For reasons of length, only compounds containing a maximum of seven condensed rings have been considered, with a few exceptions.

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Section: Pyrido[32‐a]acridine {Benzo[b][47]phenanthroline}mentioning

confidence: 99%

Section: Pyrido[32-a]acridine {Benzo[b][47]phenanthroline}mentioning

confidence: 99%

Section: Pyrido[32-a]acridine {Benzo[b][47]phenanthroline}mentioning

confidence: 99%

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Pyridoacridines in the 21st Century

Joule

Álvarez

2019

Eur J Org Chem

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“…[22,23,25,26,46,[49][50][51] In addition to their spectroscopic and electrochemical characterization, nearly two-thirds of them have also been studied by single-crystal X-ray diffraction and have had their EAsd etermined by low-temperature gas-phase photoelectron spectroscopy.T hese strong electron acceptors, with EAst hat range from 1.8 to 3.2 eV,a re listed in Supporting Information Ta ble S1.T his table also includes information about the 16 other PAH(CF 3 ) n derivatives reported by others that were prepared by more conventional, multi-steps ynthetic methods. [28,[52][53][54][55][56][57][58][59][60][61][62][63] We herein report as olution, solid-state, and computational study of nine (PAH) x /(PAH(CF 3 ) n ) y donor/acceptor (D/A) chargetransfer (CT) complexes that involve the four PAHd onors and six PAH(CF 3 ) n acceptors shown in Figure 1a nd Figure2,r espectively.T heir abbreviations, ionization energies (IEs), EAs, E 1/2 (+ /0) or E 1/2 (0/À)e lectrochemical potentials, and longest wavelength CT l max valuesa re listed in Table 1. [64][65][66] These are the first D/A CT complexes with PAH(CF 3 ) n acceptors to be studied in detail.T he nine D/A combinations werec hosen to allow several comparisons to be made in order to providen ew insights about controlling PAHD /A interactions and the structures of CT co-crystals.…”

Section: Introductionmentioning

confidence: 99%

“…These strong electron acceptors, with EA s that range from 1.8 to 3.2 eV, are listed in Supporting Information Table S1. This table also includes information about the 16 other PAH(CF 3 ) n derivatives reported by others that were prepared by more conventional, multi‐step synthetic methods …”

Section: Introductionmentioning

confidence: 99%

PAH/PAH(CF₃)_n Donor/Acceptor Charge‐Transfer Complexes in Solution and in Solid‐State Co‐Crystals

Castro

Bukovsky

Kuvychko

et al. 2019

Chemistry A European J

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A solution, solid‐state, and computational study is reported of polycyclic aromatic hydrocarbon PAH/PAH(CF3)n donor/acceptor (D/A) charge‐transfer complexes that involve six PAH(CF3)n acceptors with known gas‐phase electron affinities that range from 2.11(2) to 2.805(15) eV and four PAH donors, including seven CT co‐crystal X‐ray structures that exhibit hexagonal arrays of mixed π‐stacks with 1/1, 1/2, or 2/1 D/A stoichiometries (PAH=anthracene, azulene, coronene, perylene, pyrene, triphenylene; n=5, 6). These are the first D/A CT complexes with PAH(CF3)n acceptors to be studied in detail. The nine D/A combinations were chosen to allow several structural and electronic comparisons to be made, providing new insights about controlling D/A interactions and the structures of CT co‐crystals. The comparisons include, among others, CT complexes of the same PAH(CF3)n acceptor with four PAH donors and CT complexes of the same donor with four PAH(CF3)n acceptors. All nine CT complexes exhibit charge‐transfer bands in solution with λ max between 467 and 600 nm. A plot of E(λ max) versus [IE(donor)−EA(acceptor)] for the nine CT complexes studied is linear with a slope of 0.72±0.03 eV eV−1. This plot is the first of its kind for CT complexes with structurally related donors and acceptors for which precise experimental gas‐phase IEs and EAs are known. It demonstrates that conclusions based on the common assumption that the slope of a CT E(λ max) versus [IE−EA] plot is unity may be incorrect in at least some cases and should be reconsidered.

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Aryne Insertion into σ Bonds

Asamdi

Chikhalia

2017

Asian J Org Chem

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The synthesis of aryne intermediates from ortho‐(trimethylsilyl)aryl triflates by employing a fluoride source, first reported by Kobayashi′s group, has provided a new avenue for the simultaneous construction of two sigma bonds on a benzene ring by inserting an aryne into the sigma bond in a more‐convenient manner. The generation of ortho‐substituted benzenes through aryne intermediates offers a potent scaffold for the synthesis of bioactive heterocyclic compounds, ligands, and natural products. The main aim of this Focus Review is to highlight the application of Kobayashi′s aryne precursor to the one‐pot synthesis of ortho‐substituted benzenes. Examples include transformations that employ transition‐metal catalysis and those that do not.

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Facile synthetic protocols for perfluoroalkyl-substituted diazapentaphenes

Cited by 14 publications

References 26 publications

Pyridoacridines in the 21st Century

Pyridoacridines in the 21st Century

PAH/PAH(CF₃)_n Donor/Acceptor Charge‐Transfer Complexes in Solution and in Solid‐State Co‐Crystals

Aryne Insertion into σ Bonds

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Facile synthetic protocols for perfluoroalkyl-substituted diazapentaphenes

Cited by 14 publications

References 26 publications

Pyridoacridines in the 21st Century

Pyridoacridines in the 21st Century

PAH/PAH(CF3)n Donor/Acceptor Charge‐Transfer Complexes in Solution and in Solid‐State Co‐Crystals

Aryne Insertion into σ Bonds

Contact Info

Product

Resources

About

PAH/PAH(CF₃)_n Donor/Acceptor Charge‐Transfer Complexes in Solution and in Solid‐State Co‐Crystals