59115-44-5Relevant academic research and scientific papers
Nickel Carbodicarbene Catalyzes Kumada Cross-Coupling of Aryl Ethers with Grignard Reagents through C–O Bond Activation
Ambre, Ram,Yang, Hsuan,Chen, Wen-Ching,Yap, Glenn P. A.,Jurca, Titel,Ong, Tiow-Gan
supporting information, p. 3511 - 3517 (2019/08/12)
The development of a cross-coupling reaction protocol between aryl ethers and Grignard reagents catalyzed by carbodicarbene (CDC) nickel complexes to afford biaryl compounds through C–O cleavage is reported. Aromatic substrates featuring a broad range of electron neutral, donating, or withdrawing groups are introduced at the desired position. The method has proven effective over a wide range of naphthyl methyl ethers, anisoles, and Grignard reagents. The robustness of the protocol is validated by performing multiple cleavage reactions, gram scale synthesis, and arylation of a dimethoxy esterdiol derivative.
Chromium-Catalyzed Regioselective Kumada Arylative Cross-Coupling of C(aryl)-O Bonds with a Traceless Activation Strategy
Fan, Fei,Tang, Jinghua,Luo, Meiming,Zeng, Xiaoming
, p. 13549 - 13559 (2018/10/31)
We report here the chromium-catalyzed regioselective Kumada arylative cross-coupling of C(aryl)-O bonds at ambient temperature. By using a simple and low-cost chromium(II) chloride salt as a precatalyst, accompanied by a 2-pyridyl ligation, the catalytic cleavage and arylative coupling of C(aryl)-O bonds were achieved with a traceless activation strategy, overcoming the regioselectivity obstacle when several C-O bonds coexist in the Kumada coupling system.
NOVEL HETEROCYCLIC COMPOUND, METHOD FOR PRODUCING INTERMEDIATE THEREFOR, AND USE THEREOF
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Paragraph 0130, (2014/01/17)
Provided are a novel heterocyclic compound represented by formula (1), and a field-effect transistor having a semiconductor layer comprising the aforementioned compound. Also provided is a method for producing an intermediate enabling the production of th
The role of gold acetylides as a selectivity trigger and the importance of gem-diaurated species in the gold-catalyzed hydroarylating-aromatization of arene-diynes
Stephen,Hashmi,Braun, Ingo,Rudolph, Matthias,Rominger, Frank
scheme or table, p. 644 - 661 (2012/04/10)
Terminal 1,2-dialkynylarenes undergo an unexpected cyclization hydroarylation reaction toward naphthalene derivatives in benzene as the solvent. The regioselectivity of the reaction can be controlled by careful catalyst tuning. Also, the preparation of a bench-stable cationic amine complex or simple heterogenization of the catalyst on neutral aluminum oxide, which enables efficient catalyst recycling, was possible. Intensive mechanistic investigations were undertaken, giving new insights into the so-far underestimated role of acetylides in gold chemistry. The gold plays a fascinating dual role serving to both catalyze the reaction and activate the substrate by AuC-bond formation. Evidence of gem-diaurated compounds playing an important part for gold catalysis is also reported.
General synthesis of dinaphtho[2,3- b:2′,3′- f ]thieno[3,2- b ]thiophene (DNTT) derivatives
Niimi, Kazuki,Kang, Myeong Jin,Miyazaki, Eigo,Osaka, Itaru,Takimiya, Kazuo
supporting information; experimental part, p. 3430 - 3433 (2011/08/22)
A new straightforward synthesis of dinaphtho[2,3-b:2′,3′-f] thieno[3,2-b]thiophene (DNTT) derivatives from readily available 2-methoxynaphthalenes is described. Thus, newly developed derivatives of DNTT showed very high field effect mobility in the vapor-
Cross-coupling of aryl/alkenyl pivalates with organozinc reagents through nickel-catalyzed C-O bond activation under mild reaction conditions
Li, Bi-Jie,Li, Yi-Zhou,Lu, Xing-Yu,Liu, Jia,Guan, Bing-Tao,Shi, Zhang-Jie
supporting information; experimental part, p. 10124 - 10127 (2009/05/30)
Finding the right partner: The catalyst system [NiCl2(PCy 3)2] mediates the title transformation with high efficiency and allows aryl-aryl and vinyl-aryl coupling to proceed. The first example of catalytic cross-coupling u
ERβ ligands. 3. Exploiting two binding orientations of the 2-phenylnaphthalene scaffold to achieve ERβ selectivity
Mewshaw, Richard E.,Edsall Jr., Richard J.,Yang, Cuijian,Manas, Eric S.,Xu, Zhang B.,Henderson, Ruth A.,Keith Jr., James C.,Harris, Heather A.
, p. 3953 - 3979 (2007/10/03)
The 2-phenylnaphthalene scaffold was explored as a simplified version of genistein in order to identify ER selective ligands. With the aid of docking studies, positions 1, 4, and 8 of the 2-phenylnaphthalene template were predicted to be the most potentially influential positions to enhance ER selectivity using two different binding orientations. Both orientations have the phenol moiety mimicking the A-ring of genistein. Several compounds predicted to adopt orientations similar to that of genistein when bound to ERβ were observed to have slightly higher ER affinity and selectivity than genistein. The second orientation we exploited, which was different from that of genistein when bound to ERβ, resulted in the discovery of several compounds that had superior ER selectivity and affinity versus genistein. X-ray structures of two ER selective compounds (i.e., 15 and 47) confirmed the alternate binding mode and suggested that substituents at positions 1 and 8 were responsible for inducing selectivity. One compound (i.e., 47, WAY-202196) was further examined and found to be effective in two models of inflammation, suggesting that targeting ER may be therapeutically useful in treating certain chronic inflammatory diseases.
