- Palladium-Catalyzed Ligand-Controlled Regioselective Nucleophilic Aromatic Substitution of 1-(Chloromethyl)naphthalenes with Arylacetonitriles
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The palladium-catalyzed reaction of 1-(chloromethyl)naphthalenes 1 with (hetero)arylacetonitriles 2 gives either para- or ortho-acylated naphthalenes (3 or 4) in good to high yields. The regioselectivity can be controlled by the ligand of a palladium catalyst. A sterically bulky ligand, tBuPPh2, affords para-acylated products 3, whereas a sterically less bulky ligand, Me2PPh, provides ortho-acylated products 4. Further, direct substitution product 5 at the benzylic position is not obtained essentially, although such a reaction at the benzylic position is favorable in ordinary nucleophilic substitutions. In this paper, it was revealed that the benzylpalladium intermediate could react through a different mode (η3-benzylpalladium intermediate or η1-benzylpalladium intermediate) in nucleophilic aromatic substitution. In addition to the interesting mechanistic aspect, the present reaction provides a facile synthetic method for a wide range of diaryl ketones, some of which are not easily available through the previously known procedures.
- Zhang, Sheng,Yamamoto, Yoshinori,Bao, Ming
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p. 13981 - 13990
(2018/11/30)
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- Ruthenium-Catalyzed Cycloisomerization of 2-Alkynylstyrenes via 1,2-Carbon Migration That Leads to Substituted Naphthalenes
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A ruthenium-catalyzed carbocyclization of 2-alkynylstyrenes that involves a very rare 1,2-carbon migration of internal alkynes is reported. Various 1,2-di -and 1,4,7-trisubstituted naphthalenes are synthesized. Mechanistic studies revealed that this reaction proceeds via a disubstituted vinylidene complex as the key intermediate by 1,2-carbon migration of the 2-alkynylstyrenes.
- Watanabe, Takuma,Abe, Haruka,Mutoh, Yuichiro,Saito, Shinichi
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supporting information
p. 11545 - 11549
(2018/08/17)
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- Synthesis and structural characterization of Pd(II) thiosemicarbazonato complex: Catalytic evaluation in synthesis of diaryl ketones from aryl aldehydes and arylboronic acids
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A simple route to synthesize triphenylphosphinopalladium(II) thiosemicarbazonato complex has been described. Elemental analysis, spectral (IR, NMR) and single crystal X-ray diffraction techniques were employed for the complete characterization of the complex. The latter was found to be effective catalyst for carbon–carbon cross-coupling reaction of aryl- and heteroarylboronic acids with aromatic and heteroaromatic aldehydes to form the corresponding diaryl ketones. The influence of reaction parameters such as solvent, base, reaction temperature and catalyst loading was also investigated.
- Prabhu, Rupesh Narayana,Ramesh, Rengan
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supporting information
p. 405 - 409
(2017/01/10)
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- CARBONYLPHENACENE COMPOUND, ORGANIC LUMINESCENT MATERIAL, ORGANIC SEMICONDUCTOR MATERIAL AND METHOD OF PRODUCING CARBONYLPHENACENE COMPOUND
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PROBLEM TO BE SOLVED: To provide novel compounds which have resistance to external environments, such as high voltages and oxygen, and are usable in organic semiconductor materials, etc. and a method of producing such novel compounds efficiently. SOLUTION
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Paragraph 0051; 0052
(2016/10/07)
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- Gold-catalyzed reactions of enynals/enynones with norbornenes: Generation and trapping of cyclic o-quinodimethanes (o-QDMs)
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Fan-like structures: An efficient AuIII-catalyzed method to generate the highly reactive cyclic o-quinodimethane (o-QDM) species from easily available enynals or enynones is presented (see scheme). This method produced a variety of structurally unique fan-like products with the advantages of mild reaction conditions, excellent diastereoselectivities, and high functional-group tolerance. Copyright
- Zhu, Shifa,Zhang, Zhicai,Huang, Xiaobing,Jiang, Huanfeng,Guo, Zhengjiang
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supporting information
p. 4695 - 4700
(2013/05/09)
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- Tf2O as a rapid and efficient promoter for the dehydrative Friedel-Crafts acylation of aromatic compounds with carboxylic acids
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The Friedel-Crafts acylation of aromatic compounds with carboxylic acids was investigated in the presence of Tf2O. The reaction was carried out efficiently and very rapidly under mild reaction conditions without the need of any catalyst.
- Khodaei, Mohammd Mehdi,Alizadeh, Abdolhamid,Nazari, Ehsan
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p. 4199 - 4202
(2008/02/05)
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- Acylation of naphthalenes and anthracene on sulfated zirconia
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Sulfated zirconia (SZ) exhibits a high catalytic performance in the benzoylation of 1-methoxynaphthalene. Therefore, it was used as heterogeneous catalyst in the acylation of methoxynaphthalenes, methylnaphthalenes, naphthalene, and anthracene with benzoic anhydride, benzoyl chloride, and acetic anhydride to synthesize aromatic ketones. The rate of product formation on SZ was dependent on the respective aromatic, on the solvent used, and on the ratio of aromatic to acylating agent.
- Deutsch,Prescott,Mueller,Kemnitz,Lieske
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p. 269 - 278
(2007/10/03)
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- Activation of bismuth(III) derivatives in ionic liquids: Novel and recyclable catalytic systems for Friedel-Crafts acylation of aromatic compounds
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(Matrix presented) The activity of four bismuth(III) derivatives when employed as Friedel-Crafts catalysts for the acylation of aromatics was found to increase dramatically when dissolved in ionic liquids. Solutions of bismuth oxide or triflate in [emim][NTf2] and [bmim][NTf2] are the most efficient catalytic systems, with catalyst loading as low as 1% leading to clean, high-yielding acylation of a variety of benzene derivatives. These improved Friedel-Crafts catalytic systems can also be efficiently recycled as opposed to traditional systems.
- Gmouh, Said,Yang, Hongly,Vaultier, Michel
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p. 2219 - 2222
(2007/10/03)
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