22187-13-9Relevant academic research and scientific papers
An alternative method for generating arynes from ortho-silylaryl triflates: Activation by cesium carbonate in the presence of a crown ether
Yoshida, Suguru,Hazama, Yuki,Sumida, Yuto,Yano, Takahisa,Hosoya, Takamitsu
, p. 10131 - 10140 (2015)
An alternative method for generating arynes from ortho-silylaryl triflates using cesium carbonate and 18-crown-6 is reported. The method was efficiently applied to a variety of reactions between several arynes and arynophiles. We also demonstrated that the efficiency of aryne generation is significantly affected by the alkali metal countercation of the carbonate.
Rapid access to substituted 2-naphthyne intermediates: Via the benzannulation of halogenated silylalkynes
Hein, Samuel J.,Lehnherr, Dan,Dichtel, William R.
, p. 5675 - 5681 (2017)
Aryne intermediates are versatile and important reactive intermediates for natural product and polymer synthesis. 2-Naphthynes are relatively unexplored because few methods provide precursors to these intermediates, especially for those bearing additional substituents. Here we report a general synthetic strategy to access 2-naphthyne precursors through an Asao-Yamamoto benzannulation of ortho-(phenylethynyl)benzaldehydes with halo-silylalkynes. This transformation provides 2-halo-3-silylnaphthalenes with complete regioselectivity. These naphthalene products undergo desilylation/dehalogenation in the presence of F- to generate the corresponding 2-naphthyne intermediate, as evidenced by furan trapping experiments. When these 2-naphthynes are generated in the presence of a copper catalyst, ortho-naphthalene oligomers, trinaphthalene, or binaphthalene products are formed selectively by varying the catalyst loading and reaction temperature. The efficiency, mild conditions, and versatility of the naphthalene products and naphthyne intermediates will provide efficient access to many new functional aromatic systems.
2, 3, 6, 7 -pentycene tetracarboxylic dianhydride compound and synthesis method thereof
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Paragraph 0140; 0145-0150; 0209; 0214-0219, (2020/06/27)
The invention discloses a 2,3,6,7-pentaptycene tetracarboxylic dianhydride compound and a synthetic method thereof. The method comprises three stages. In the first stage, 2,3,6,7-tetramethyl-9,10-p-(2,3-anthryl)anthracene is synthesized; in the second stage, 2,3,6,7-pentaptycene tetracarboxylic acid is synthesized; and in the third stage, 2,3,6,7-pentaptycene tetracarboxylic dianhydride is synthesized. The method is cheap and available in raw materials and high in yield, the purity of products is high, and pentaptycene dianhydride can be efficiently synthesized at low cost. Compared with a series of new polyimide macromolecular materials polymerized from a diamine monomer in the prior art, the compound has great potential application value in the fields of membrane separation materials, dielectric materials and molecular interlocking functional materials.
One-pot synthesis of benzo[: B] fluorenones via a cobalt-catalyzed MHP-directed [3+2] annulation/ring-opening/dehydration sequence
Qiu, Shuxian,Zhai, Shengxian,Wang, Huifei,Chen, Xiaoming,Zhai, Hongbin
supporting information, p. 4206 - 4209 (2019/04/30)
We have developed a one-pot synthesis of benzo[b]fluorenones via a cobalt-catalyzed [3+2] annulation of oxabicyclic alkenes followed by a ring-opening/dehydration sequence in good to excellent yields. With the use of 2-(1-methylhydrazinyl)pyridine (MHP),
Aryne cycloaddition reactions of benzodioxasilines as aryne precursors generated by catalytic reductive ortho-C[sbnd]H silylation of phenols with traceless acetal directing groups
Asgari, Parham,Dakarapu, Udaya Sree,Nguyen, Hiep H.,Jeon, Junha
, p. 4052 - 4061 (2017/06/29)
Diversely substituted arylsilyl triflates, as aryne precursors for aryne cycloaddition reactions, were accessed from benzodioxasilines. Catalytic reductive C[sbnd]H ortho-silylation of phenols with traceless acetal directing groups was exploited to prepare benzodioxasilines. Sequential addition of MeLi and then trifluoromethanesulfonic anhydride to benzodioxasilines provided arylsilyl triflates in a single pot. Notably, this approach was successfully utilized to prepare sterically hindered 1,2,3-trisubstituted arylsilyl triflates, which ultimately underwent fluoride-mediated aryne cycloaddition.
Improved and practical synthesis of [2,4,5-tris(trimethylsilyl)- Phenyl](phenyl)iodonium triflate and utilization as a 1,4-benzdiyne synthon
Gondo, Keisuke,Kitamura, Tsugio
, p. 2107 - 2112 (2014/07/07)
An efficient and improved method for preparing [2,4,5-tris(trimethylsilyl) phenyl](phenyl)iodonium triflate as a 1,4-benzdiyne synthon was developed by using phenyiodonium diacetate/boron triflouride diethyl etherate [PhI(OAc) 2/BF3 OEt2] reagent. The iodonium triflate generated 3,4-bis(trimethylsilyl)benzyne quantitatively to give cycloadducts with tetraphenylcyclopentadienone, furan and anthracene in high yields. These cycloadducts bearing two trimethylsilyl groups were transformed into the corresponding aryne precursors, which underwent subsequent cycloaddition reactions to afford polycyclic aromatic compounds such as 1,4-dihydro-1,4- epoxyanthracene, naphthotriazole, triptycene, and anthratriazole derivatives in good to high yields. The total reactions are formally considered as double cycloaddition reactions of 1,4-benzdiyne. This practical and useful formal benzdiyne strategy is described.
Synthesis and characterization of oxadisilole-fused 1H-benzo[f]indazoles and 1H-naphtho[2,3-f]indazoles
Zhang, Yajuan,Ma, Xuyan,Chen, Yali,Chen, Xuanming,Guo, Lei,Cao, Weiguo,Chen, Jie,Wong, Man Shing
, p. 3005 - 3012 (2013/06/26)
Oxadisilole-fused 1H-benzo[f]- and 1H-naphtho[2,3-f]indazoles have been synthesized by the 1,3-dipolar cycloaddition reactions of benzo- or naphtho-oxabicycloalkenes with nitrile imines generated in situ from N-arylhydrazonoyl chlorides followed by deoxygenation and aromatization. The photophysical, redox and thermal properties of these compounds have been characterized. Some of the indazoles show potential as deep-blue emitters for OLED applications as a result of their high fluorescence quantum yields and good thermal stabilities. Oxadisilole-fused 1H-benzo[f]- and 1H-naphtho[2,3-f] indazoles have been synthesized by the 1,3-dipolar cycloaddition of benzo- or naphtho-oxabicycloalkenes with nitrile imines followed by deoxygenation and aromatization. Their photophysical, redox and thermal properties show that some of the indazoles show potential as deep-blue emitters for OLED applications. Copyright
Synthesis and characterization of oxadisilole-fused-3,4-dihydro-2H- naphtho[2,1-e]-1,3-oxazines and 3,4-dihydro-2H-anthra[2,1-e]-1,3-oxazines
Xu, Di,Lin, Yibei,Chen, Yali,Zhang, Jie,Cao, Weiguo,Chen, Jie,Wong, Man Shing
, p. 6144 - 6149 (2013/07/27)
Oxadisilole-fused-3,4-dihydro-2H-naphtho[2,1-e]-1,3-oxazines and 3,4-dihydro-2H-anthra[2,1-e]-1,3-oxazines were synthesized through an eco-friendly Mannich type condensation-cyclization reaction of oxadisilole-fused-1-naphthalenol or 1-anthracenol with fo
Generation of synthetic equivalents of benzdiynes from benzobisoxadisiloles
Chen, Ya-Li,Sun, Jiang-Qin,Wei, Xin,Wong, Wai-Yeung,Lee, Albert W. M.
, p. 7190 - 7197 (2007/10/03)
Linear and angular benzobisoxadisiloles 14 and 16 can serve as the precursors for stepwise generations of the syntetic equivalents of 1,4- and 1,3-benzdiynes. Benzynes generated were trapped as [4+2] cycloaddition products. Two identical or different ring
Cycloaddition reactions of benzynes generated from benzobisoxadisilole, benzotrisoxadisilole and naphthoxadisilole
Chen, Ya-Li,Zhang, Hong-Kui,Wong, Wai-Yeung,Lee, Albert W.M
, p. 2259 - 2262 (2007/10/03)
Benzynes (7, 16) generated from benzobisoxadisilole and benzotrisoxadisilole were trapped as the furan cycloaddition adducts. Naphthoxadisilole and naphthobisoxadisilole were also synthesized.
