- A novel and efficient synthesis of phenanthrene derivatives via palladium/norbornadiene-catalyzed domino one-pot reaction
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Herein we report a novel palladium-catalyzed reaction that results in phenanthrene derivatives using aryl iodides, ortho-bromoben-zoyl chlorides and norbornadiene in one pot. This dramatic transformation undergoes ortho-C–H activation, decarbonylation and subsequent a retro-Diels–Alder process. Pleasantly, this protocol has a wider substrate range, shorter reaction times and higher yields of products than previously reported methods.
- Zhong, Yue,Wu, Wen-Yu,Yu, Shao-Peng,Fan, Tian-Yuan,Yu, Hai-Tao,Li, Nian-Guang,Shi, Zhi-Hao,Tang, Yu-Ping,Duan, Jin-Ao
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supporting information
p. 291 - 298
(2019/02/20)
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- Regioselective Synthesis of Polycyclic and Heptagon-embedded Aromatic Compounds through a Versatile π-Extension of Aryl Halides
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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.
- Fu, Wai Chung,Wang, Zheng,Chan, Wesley Ting Kwok,Lin, Zhenyang,Kwong, Fuk Yee
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supporting information
p. 7166 - 7170
(2017/06/13)
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- [4 + 2] Annulation of Donor-Acceptor Cyclopropanes with Acetylenes Using 1,2-Zwitterionic Reactivity
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A new process for the [4 + 2] annulation of donor-acceptor cyclopropanes with acetylenes under the effect of anhydrous GaCl3 using 1,2-zwitterion reactivity was elaborated. The reaction opens access to substituted dihydronaphthalenes, naphthalenes, and other fused carbocycles. The direction of the reaction can be efficiently controlled by temperature.
- Novikov, Roman A.,Tarasova, Anna V.,Denisov, Dmitry A.,Borisov, Denis D.,Korolev, Victor A.,Timofeev, Vladimir P.,Tomilov, Yury V.
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p. 2724 - 2738
(2017/03/14)
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- Bismuth-catalyzed synthesis of polycyclic aromatic hydrocarbons (PAHs) with a phenanthrene backbone via cyclization and aromatization of 2-(2-arylphenyl)vinyl ethers
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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.
- Murai, Masahito,Hosokawa, Naoki,Roy, David,Takai, Kazuhiko
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supporting information
p. 4134 - 4137
(2014/09/30)
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- A convergent approach to polycyclic aromatic hydrocarbons
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A new concise route to Polycyclic Aromatic Hydrocarbons (PAHs) through radical addition and cyclisation of xanthates is described. The Royal Society of Chemistry 2011.
- Guignard, Raphael F.,Zard, Samir Z.
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supporting information; experimental part
p. 12185 - 12187
(2011/12/15)
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- Characterization of the combustion products of polyethylene
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Polyethylene (PE) was burned in a tube-type furnace with an air flow at a temperature of 600~900°C. Combustion products were collected with glass wool, glass fiber filter, and XAD-2 adsorbent. The analysis of the products was performed with GC-FID and GC-MSD. At low temperature, hydrocarbons were the major components, while at higher temperature the products were composed of polycyclic aromatic hydrocarbons. With the high performance of the Hewlett-Packard 6890GC-5973MSD, more compounds were identified in comparison with previous studies.
- Piao, Mingjun,Chu, Shaogang,Zheng, Minghui,Xu, Xiaobai
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p. 1497 - 1512
(2007/10/03)
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