13837-48-4Relevant academic research and scientific papers
Modular Design of Fluorescent Dibenzo- and Naphtho-Fluoranthenes: Structural Rearrangements and Electronic Properties
Mohammad-Pour, Gavin S.,Ly, Richard T.,Fairchild, David C.,Burnstine-Townley, Alex,Vazquez-Molina, Demetrius A.,Trieu, Khang D.,Campiglia, Andres D.,Harper, James K.,Uribe-Romo, Fernando J.
, p. 8036 - 8053 (2018)
A library of 12 dibenzo- and naphtho-fluoranthene polycyclic aromatic hydrocarbons (PAHs) with MW = 302 (C24H14) was synthesized via a Pd-catalyzed fluoranthene ring-closing reaction. By understanding the various modes by which the palladium migrates during the transformation, structural rearrangements were bypassed, obtaining pure PAHs in high yields. Spectroscopic and electrochemical characterization demonstrated the profound diversity in the electronic structures between isomers. Highlighting the significant differences in emission of visible light, this library of PAHs will enable their standardization for toxicological assessment and potential use as optoelectronic materials.
Regioselective Synthesis of Polycyclic and Heptagon-embedded Aromatic Compounds through a Versatile π-Extension of Aryl Halides
Fu, Wai Chung,Wang, Zheng,Chan, Wesley Ting Kwok,Lin, Zhenyang,Kwong, Fuk Yee
, p. 7166 - 7170 (2017)
A versatile π-extension reaction was developed based on the three-component cross-coupling of aryl halides, 2-haloarylcarboxylic acids, and norbornadiene. The transformation is driven by the direction and subsequent decarboxylation of the carboxyl group, while norbornadiene serves as an ortho-C?H activator and ethylene synthon via a retro-Diels–Alder reaction. Comprehensive DFT calculations were performed to account for the catalytic intermediates.
Synthesis of substituted phenanthrenes via intramolecular condensation based on temperature-dependent deprotonation using a weak carbonate base
Monsieurs, Katrien,Rombouts, Geert,Tapolcsányi, Pál,Mátyus, Péter,Maes, Bert U. W.
, p. 3225 - 3230 (2006)
Construction of substituted phenanthrenes via intramolecular condensation of 2′-methylbiphenyl-2-carbaldehydes using a mild base at 200 °C is described. The required high temperature can be quickly reached and easily maintained using microwave flash heating. Georg Thieme Verlag Stuttgart.
Synthesis of phenanthrene and alkyl phenanthrenes by palladium(0)-catalyzed pericyclic reactions
Jana, Rathin,Biswas, Anup,Samanta, Shubhankar,Ray, Jayanta K.
, p. 2092 - 2100 (2010)
Palladium-catalyzed pericyclic reactions have been developed for the synthesis of phenanthrenes. This method is also useful for the synthesis of monoalkyl and dialkyl phenanthrene derivatives. Georg Thieme Verlag Stuttgart.
Synthesis of phenanthrenes by cationic chromium(III) porphyrin-catalyzed dehydration cycloaromatization
Wakabayashi, Ryota,Kurahashi, Takuya,Matsubara, Seijiro
, p. 2297 - 2301 (2013)
Readily available biphenyl derivatives with ortho oxirane moiety react in the presence of cationic chromiun(III) porphyrin catalyst to afford phenanthrenes. The reaction is considered to be triggered by activation of the oxirane moiety through coordination to the Lewis acidic cationic chromium to give aldehyde via 1,2-hydride shift, which reacts with arene through intramolecular electrophilic aromatic substitution and subsequent dehydration. The reaction allows constructing a variety of polycyclic aromatic and heteroaromatic compounds.
Br?nsted Acid-Catalyzed Carbonyl-Olefin Metathesis: Synthesis of Phenanthrenes via Phosphomolybdic Acid as a Catalyst
Chen, Yi,Liu, Di,Wang, Rui,Xu, Li,Tan, Jingyao,Shu, Mao,Tian, Lingfeng,Jin, Yuan,Zhang, Xiaoke,Lin, Zhihua
, p. 351 - 362 (2022/01/03)
Compared with the impressive achievements of catalytic carbonyl-olefin metathesis (CCOM) mediated by Lewis acid catalysts, exploration of the CCOM through Br?nsted acid-catalyzed approaches remains quite challenging. Herein, we disclose a synthetic protocol for the construction of a valuable polycycle scaffold through the CCOM with the inexpensive, nontoxic phosphomolybdic acid as a catalyst. The current annulations could realize carbonyl-olefin, carbonyl-alcohol, and acetal-alcohol in situ CCOM reactions and feature mild reaction conditions, simple manipulation, and scalability, making this strategy a promising alternative to the Lewis acid-catalyzed COM reaction.
Oxidative, Iodoarene-Catalyzed Intramolecular Alkene Arylation for the Synthesis of Polycyclic Aromatic Hydrocarbons
Zhao, Zhensheng,Britt, Liam H.,Murphy, Graham K.
, p. 17002 - 17005 (2018/11/01)
A catalytic, metal-free and chemoselective oxidative intramolecular coupling of arene and alkene C?H bonds is reported. The active hypervalent iodine (HVI) reagent, generated catalytically in situ from iodotoluene and meta-chloroperoxybenzoic acid (m-CPBA), reacts with o-vinylbiphenyls to generate polyaromatic hydrocarbons in up to 95 % yield. Experimental evidence suggests the reactions proceed though vinyliodonium and, possibly, vinylenephenonium intermediates.
Facile Synthesis of Polycyclic Aromatic Hydrocarbons: Br?nsted Acid Catalyzed Dehydrative Cycloaromatization of Carbonyl Compounds in 1,1,1,3,3,3-Hexafluoropropan-2-ol
Fujita, Takeshi,Takahashi, Ikko,Hayashi, Masaki,Wang, Jingchen,Fuchibe, Kohei,Ichikawa, Junji
supporting information, p. 262 - 265 (2017/01/24)
The cycloaromatization of aromatic aldehydes and ketones was readily achieved by using a Br?nsted acid catalyst in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP). In the presence of a catalytic amount of trifluoromethanesulfonic acid, biaryl-2-ylacetaldehydes and 2-benzylbenzaldehydes underwent sequential intramolecular cationic cyclization and dehydration to afford phenacenes and acenes, respectively. Furthermore, biaryl-2-ylacetaldehydes bearing a cyclopentene moiety at the α-position underwent unprecedented cycloaromatization including ring expansion to afford triphenylenes. HFIP effectively promoted the cyclizations by suppressing side reactions presumably as a result of stabilization of the cationic intermediates.
A combined experimental and computational study on the cycloisomerization of 2-ethynylbiaryls catalyzed by dicationic arene ruthenium complexes
Yamamoto, Yoshihiko,Matsui, Kazuma,Shibuya, Masatoshi
supporting information, p. 7245 - 7255 (2015/05/05)
Ruthenium-catalyzed cycloisomerization of 2-ethynylbiaryls was investigated to identify an optimal ruthenium catalyst system. A combination of [η6-(p-cymene)RuCl2(PR3)] and two equivalents of AgPF6 effectively converted 2-ethynylbiphenyls into phenanthrenes in chlorobenzene at 120 °C over 20 h. Moreover, 2-ethynylheterobiaryls were found to be favorable substrates for this ruthenium catalysis, thus achieving the cycloisomerization of previously unused heterocyclic substrates. Moreover, several control experiments and DFT calculations of model complexes were performed to propose a plausible reaction mechanism.
Bismuth-catalyzed synthesis of polycyclic aromatic hydrocarbons (PAHs) with a phenanthrene backbone via cyclization and aromatization of 2-(2-arylphenyl)vinyl ethers
Murai, Masahito,Hosokawa, Naoki,Roy, David,Takai, Kazuhiko
supporting information, p. 4134 - 4137 (2014/09/30)
The reaction of 2-(2-arylphenyl)vinyl ethers in the presence of a catalytic amount of bismuth(III) triflate gave substituted phenanthrenes in excellent yields under mild reaction conditions. The reaction was also applied to the construction of other polycyclic aromatic hydrocarbons (PAHs), such as chrysene, helicene, and pyrene having a phenanthrene backbone, via regioselective cyclization. This method has the advantages of easy availability of the cyclization precursors, operational simplicity, and high reaction efficiency.
