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217-59-4Relevant articles and documents
Buu-Hoi,N.P.,Saint-Ruf,G.
, p. 2996 - 2997 (1961)
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Blum-Bergmann
, p. 1999 (1938)
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An efficient synthesis of triphenylene
Fossatelli,Brandsma
, p. 756 - 756 (1992)
Triphenylene (1) has been obtained in 66% yield by decomposition of 1-fluoro-2-sodiobenzene. The corresponding ortho-lithio, potassio and caesio compounds gave mainly other, unidentified products.
Gold-catalyzed cyclotrimerization of arynes for the synthesis of triphenylenes
Chen, Lili,Zhang, Changyuan,Wen, Chunxiao,Zhang, Kun,Liu, Wenfeng,Chen, Qian
, p. 81 - 84 (2015)
A novel and efficient Au(I)-catalyzed cyclotrimerization of arynes, generated by fluoride-induced elimination of Kobayashi's silylaryl triflates, is described. The reactions led to the formation of triphenylenes in 45-88% yields under mild conditions.
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Hansch,Geiger
, p. 477 (1958)
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Synthesis of Tribenzo[ b, d, f]azepines via Cascade π-Extended Decarboxylative Annulation Involving Cyclic Diaryliodonium Salts
Hu, Tao,Ye, Zenghui,Zhu, Kai,Xu, Kai,Wu, Yanqi,Zhang, Fengzhi
, p. 505 - 509 (2020)
Various functionalized tribenzo[b,d,f]azepines were prepared efficiently with the readily available 2-aminobenzoic acids and cyclic hypervalent diaryliodonium reagents as starting materials under Pd(II) catalysis. The key of this step-economical protocol is that the carboxylic acid functionality was employed as both a traceless directing group for the N-H activation/arylation and a functional handle for the tandem π-extended decarboxylative annulation.
Latyaeva et al.
, p. 103,108 (1969)
Pd-Catalyzed three-component coupling of terminal alkynes, arynes, and vinyl cyclopropane dicarboxylate
Garve, Lennart K. B.,Werz, Daniel B.
, p. 596 - 599 (2015)
A palladium-catalyzed three-component coupling involving in situ generated arynes, terminal alkynes, and vinyl cyclopropane dicarboxylate has been developed. The process demonstrates the first example of aryne chemistry combined with the ring opening of vinyl cyclopropanes. This efficient method using readily available starting materials generates two new carbon-carbon bonds in one pot.
Griffin,Wysocki
, p. 751 (1969)
To flip or not to flip? Assessing the inversion barrier of the tetraphenylene framework with enantiopure 2,15-dideuteriotetraphenylene and 2,7-dimethyltetraphenylene
Huang, Hui,Stewart, Timothy,Gutmann, Matthias,Ohhara, Takashi,Niimura, Nobuo,Li, Yu-Xue,Wen, Jian-Feng,Bau, Robert,Wong, Henry N. C.
, p. 359 - 369 (2009)
(Chemical Equation Presented) Two chiral tetraphenylenes, 2,15-dideuteriotetraphenylene (7) and 2,7-dimethyltetraphenylene (15) were synthesized and resolved to address the tetraphenylene inversion barrier problem. Neutron diffraction investigation of ena
Bouas-Laurent et al.
, p. 5281 (1967)
Catalytic Dehydrogenative Cyclization of o-Teraryls under pH-Neutral and Oxidant-Free Conditions
Dong, Guangbin,Tsukamoto, Tatsuhiro
, p. 15249 - 15253 (2020)
A cobaloxime-catalyzed acceptorless dehydrogenative cyclization of o-teraryls was developed. In stark contrast to the established methods such as the Scholl or Mallory reactions, this method does not require any strong acids or oxidants, and shows high atom economy and a broad substrate scope. It operates at near room temperature with light as the source of energy. Acid- or oxidant-sensitive functional groups, such as 4-methoxyphenyl, unprotected benzyl alcohol, silyl ether, and thiophene groups are tolerated. Remarkably, aryls with electron-withdrawing groups, and electron-poor heteroarenes, such as pyridine and pyrimidine, can also react. Preliminary mechanistic study reveals that hydrogen gas is released during the reaction, and both light and the cobalt catalyst are important for the dehydrogenation step.
Gilchrist,T.L. et al.
, p. 821 - 822 (1968)
Millar,Wilson
, p. 2121,2125 (1964)
Preparation of substituted triphenylenesvianickel-mediated Yamamoto coupling
LeDrew, Joshua,Maly, Kenneth E.,Schroeder, Zachary W.,Selmani, Vanessa M.
, p. 39564 - 39569 (2021/12/24)
Substituted triphenylenes show promise as organic semiconductors because of their ability to form columnar liquid crystalline phases featuring extended π-stacked arrays. While there are several methods for preparing triphenylenes, including oxidative cyclization reactions such as the Scholl reaction, as well as transition metal-catalyzed aryne cyclotrimerization, these methods are not effective for electron deficient triphenylenes. Here we demonstrate that the nickel-mediated Yamamoto coupling ofo-dibromoarenes is a concise and efficient way to prepare substituted triphenylenes, including electron-deficient systems that are otherwise challenging to prepare. We also demonstrate the application of this approach to prepare electron deficient discotic mesogens composed of triphenylenes bearing imide and thioimide groups.
Nickel-Catalyzed Homocoupling of Aryl Ethers with Magnesium Anthracene Reductant
Rawat, Vishal Kumar,Higashida, Kosuke,Sawamura, Masaya
supporting information, p. 3397 - 3403 (2021/06/28)
Nickel-catalyzed reductive homocoupling of aryl ethers has been achieved with Mg(anthracene)(thf) 3as a readily available low-cost reductant. DFT calculations provided a rationale for the specific efficiency of the diorganomagnesium-type two-electron reducing agent. The calculations show that the dianionic anthracene-9,10-diyl ligand reduces the two aryl ether substrates, resulting in the homocoupling reaction through supply of electrons to the Ni-Mg bimetallic system to form organomagnesium nickel(0)-ate complexes, which cause two sequential C-O bond cleavage reactions. The calculations also showed cooperative actions of Lewis acidic magnesium atoms and electron-rich nickel atoms in the C-O cleavage reactions.
