Controlling the Scholl Reaction

King, Benjamin T.; Kroulík, Jiří; Robertson, Charles R.; Rempała, Paweł; Hilton, Cameron L.; Korinek, Justin D.; Gortari, Lisa M.

doi:10.1021/jo061515x

Cited by 289 publications

(231 citation statements)

References 35 publications

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“…Although the mechanistic details of the reaction have not been clarified yet, strong Brønsted acids may promote protonation of the anthracene ring and electron transfer to DDQ, and arenium-type cations may be generated as intermediate species. 13,15,16 In comparison with the previous synthetic methods of the meso-substituted bisanthenes reported by Maulding,17a Wu, 17b and Scott, 17c it is noticeable that our strategy can directly and cleanly afford bisanthene from the corresponding bisanthryl in semi-gram scale.…”

mentioning

confidence: 64%

Facile Synthesis and Lateral π-Expansion of Bisanthenes

et al. 2013

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confidence: 64%

Facile Synthesis and Lateral π-Expansion of Bisanthenes

et al. 2013

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“…[20,21] A detailed comparative study of King et al supports the potential of MoCl 5 as useful reagent in Scholl-type reactions. [22] The performance is similar to that of phenyliodineA C H T U N G T R E N N U N G (III)-bistrifluoroacetate (PIFA). [23] For oxidative cyclization reactions Lewis acidic additives can be beneficial since they act as HCl trapping agents.…”

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confidence: 74%

Oxidative Coupling of Diaryldisulfides by MoCl₅ to Thianthrenes

Spurg

Schnakenburg

Waldvogel

2009

Chemistry A European J

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“…[18][19][20] Electron donating substituents both direct and promote CC bond formation under cyclodehydrogenation conditions. 21,22 Tuning the intramolecular properties of graphenes is one step in the search for technology-enabling materials. Also essential is the ability to exert some supramolecular control of structure.…”

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confidence: 99%

Methoxy functionalisation: exerting synthetic control of the supramolecular and electronic structure of nitrogen-doped nanographenes

et al. 2014

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We describe a series of functionalized N-containing heterosuperbenzenes, created with a view to investigating the strategic role of methoxy substituents in (i) promoting cyclodehydrogenation and (ii) tuning the electronic properties and (iii) the supramolecular order in the resultant fused products.The dominance of inorganic semiconductors in the manufacture of optoelectronic devices and field effect transistors is gradually being undermined by the emergence of functional organic materials. [1][2][3] Although electron mobility remains a challenge, these represent lightweight, flexible alternatives that are more readily processed using solution-based methods. Within this arena, the opportunities proffered by the exceptional electronic and physical properties of graphene and its derivatives are undeniable. [4][5][6] As many aspects in the formation of large graphitic sheets are difficult to control, synthetic chemists have pioneered routes to nanographenes with impressive and varying dimensions, and an array of peripheral substituents. 7-10 Dependent on the latter are a range of material characteristics e.g. the nature of the p-p interactions, HOMO-LUMO gaps and film-forming capabilities. [11][12][13][14] The ability to manufacture graphene systems to such specificity is notably absent in exfoliation 15 /epitaxial growth 16 processes, and this makes the further development of bottom-up synthetic methodologies for the formation of next-generation and heteroatomcontaining graphenes all the more important. 10,17 Oxidative cyclodehydrogenation is a key step in the chemical formation of planarised ring systems. All-carbon systems cyclise rapidly, while heteroatom-containing polyphenylenes appear to adopt a more complex mechanism for ring closure, e.g. both partially and fully fused species tend to be generated in a single reaction. [18][19][20] Electron donating substituents both direct and promote CC bond formation under cyclodehydrogenation conditions. 21,22 Tuning the intramolecular properties of graphenes is one step in the search for technology-enabling materials. Also essential is the ability to exert some supramolecular control of structure. Disc-like molecules tend to aggregate in columnar p-p stacks which can be either enhanced or perturbed by peripheral units e.g. long chain alkyl substituted hexaperihexabenzocoronenes frequently exhibit liquid crystalline behaviour, 2 whereas their iodo-or tert-butyl-functionalised derivatives give rise to Bernal-stacked crystalline dimers. 23 This work reveals how the combination of heteroatom doping (as pioneered by Draper et al.), 17,24-26 with H-bonding peripheral substituents, can unlock some exciting new applications for nanographene materials by controlling the outcome of the synthetic process and the HOMO-LUMO gaps and intermolecular order of the end-products.The synthetic methods used to form the precursor polyphenylenes were modifications of published routes involving cyclopentadienones (generated via two-fold Knoevenagel condensations) and their subsequent [2+4] D...

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Controlling the Scholl Reaction

Cited by 289 publications

References 35 publications

Facile Synthesis and Lateral π-Expansion of Bisanthenes

Facile Synthesis and Lateral π-Expansion of Bisanthenes

Oxidative Coupling of Diaryldisulfides by MoCl₅ to Thianthrenes

Methoxy functionalisation: exerting synthetic control of the supramolecular and electronic structure of nitrogen-doped nanographenes

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Controlling the Scholl Reaction

Cited by 289 publications

References 35 publications

Facile Synthesis and Lateral π-Expansion of Bisanthenes

Facile Synthesis and Lateral π-Expansion of Bisanthenes

Oxidative Coupling of Diaryldisulfides by MoCl5 to Thianthrenes

Methoxy functionalisation: exerting synthetic control of the supramolecular and electronic structure of nitrogen-doped nanographenes

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Oxidative Coupling of Diaryldisulfides by MoCl₅ to Thianthrenes