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217-59-4Relevant articles and documents
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.
Trialkylsilylethynyl-substituted triphenylenes and hexabenzocoronenes: Highly soluble liquid crystalline materials and their hole transport abilities
Hirose, Takuji,Miyazaki, Yutaro,Watabe, Mizuki,Akimoto, Sho,Tachikawa, Tatsuya,Kodama, Koichi,Yasutake, Mikio
, p. 4714 - 4721 (2015)
Four triphenylene (TP) and four hexa-peri-hexabenzocoronene (HBC) derivatives with trialkylsilylethynyl groups were prepared and characterized by differential scanning calorimetry, polarizing optical microscopy, and X-ray diffraction measurements. All compounds were highly soluble in less-polar organic solvents and exhibited a columnar phase, Colh or Colr for the TPs, and Colh for the HBCs. The hole transport ability in the HBCs' columnar phase, 0.4-1.5×10-3 cm2 V-1 s-1 at 40-180°C, and its temperature dependence were determined by the time-of-flight method using a solution technique.
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.
Aromatic Metamorphosis of Indoles into 1,2-Benzazaborins
Tsuchiya, Shun,Saito, Hayate,Nogi, Keisuke,Yorimitsu, Hideki
, p. 3855 - 3860 (2019)
Among the plethora of aromatic compounds, indoles represent a privileged class of substructures that is ubiquitous in natural products and pharmaceuticals. While numerous exocyclic functionalizations of indoles have provided access to a variety of useful derivatives, endocyclic transformations involving the cleavage of the C2-N bond remain challenging due to the high aromaticity and strength of this bond in indoles. Herein, we report the "aromatic metamorphosis" of indoles into 1,2-benzazaborins via the insertion of boron into the C2-N bond. This endocyclic insertion consists of a reductive ring-opening using lithium metal and a subsequent trapping of the resulting dianionic species with organoboronic esters. Considering that 1,2-azaborins have attracted increasing academic and industrial attention as BN isosteres of benzene, the counterintuitive aromatic metamorphosis presented herein can feasibly be expected to substantially advance the promising chemistry of 1,2-azaborins.
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.
C-C Bond (Hetero)arylation of Ring-Fused Benzocyclobutenols and Application in the Assembly of Polycyclic Aromatic Hydrocarbons
Mao, Wenbin,Zhu, Chen
, p. 9133 - 9143 (2017)
Herein, we disclose a new and efficient synthetic approach to triphenylene-based polycyclic aromatic hydrocarbons (PAHs) from ring-fused benzocyclobutenols (RBCBs) through the cleavage of the C-C σ-bond. Two key transformations are involved: (a) palladium-catalyzed C-C bond (hetero)arylation of RBCBs; and (b) Lewis acid-promoted intramolecular annulation leading to complex polycyclic compounds. A variety of multiply substituted triphenylenes and derivatives are obtained in synthetically useful yields.
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
Uncatalyzed zirconium-mediated biphenylation of o-dihalobenzenes to form triphenylenes
Hilton, Cameron L.,Jamison, Christopher R.,King, Benjamin T.
, p. 14824 - 14824 (2006)
The reaction of [Zr(biphe)3][(Li·(THF)4)2], where biphe is 2,2′-biphenyldiyl, with an o-dihaloarene produces a triphenylene. Two new bonds are created in this rare example of an uncatalyzed, Zr-mediated aryl-aryl bond formation. Multiple biphe fragments can be incorporated to give larger triphenylene-containing polycyclic aromatic hydrocarbons. This reaction can introduce significant strain and was demonstrated to tolerate alkyl and methoxy substituents. Copyright
Palladium-Catalyzed Regioselective Domino Spirocyclization of Carbamoyl Chlorides with Alkynes and Benzynes
Wang, Chenchen,Zhao, Wenyu,Wu, Xianqing,Qu, Jingping,Chen, Yifeng
, p. 4996 - 5001 (2020)
A palladium-catalyzed domino spiro-cyclization of carbamoyl chlorides with alkynes and benzynes, involving intramolecular C?H activation to afford valuable oxindole scaffolds bearing spiro quaternary stereocenters, has been developed. This one-step synthesis of spirooxindole is both step- and atom-economic, proceeding with high regioselectivity in moderate to excellent yields. (Figure presented.).
