154848-36-9Relevant articles and documents
Reusable Palladium N-Heterocyclic Tetracarbene for Aqueous Suzuki-Miyaura Cross-Coupling Reaction: Homogeneous Catalysis and Heterogeneous Recovery
Li, Yue,Dong, Ying,Wei, Yong-Liang,Jv, Jing-Jing,Chen, Yun-Qi,Ma, Jian-Ping,Yao, Jia-Jia,Dong, Yu-Bin
, p. 1645 - 1648 (2018)
A pH-responsive Pd(II) N-heterocyclic tetracarbene complex synthesized by a solvothermal method was reported. It can be a highly active reusable catalyst to homogeneously catalyze the Suzuki-Miyaura cross-coupling reaction in water and can be heterogeneously recovered by simply adjusting the pH value of the aqueous reaction media.
Radical Anions of Aromatic Carbonitriles as Reagents for Arylation of Fluorinated Benzonitriles
Peshkov, Roman Yu.,Wang, Chunyan,Panteleeva, Elena V.,Rybalova, Tatyana V.,Tretyakov, Evgeny V.
, (2019)
The first example of phenylation of fluorobenzonitriles with the sodium salt of a benzonitrile radical anion in liquid ammonia is presented. The reaction regioselectivity corresponds to the ortho- and para-fluorine atom substitution in fluorobenzonitrile with the phenyl moiety of the benzonitrile radical anion and affords 2- and 4-cyanobiphenyls in 40-90% yields. 3-Methoxybenzonitrile as well as 1-cyanonaphthalene radical anions were also successfully subjected to this interaction forming 3′-methoxycyanobiphenyls and (1-naphthyl)benzonitriles, respectively. The radical anion acts as an ipso-C-nucleophile with consequent loss of the cyano group. The revealed new type of radical anion reactivity opens up the prospect of developing a general approach to fluorinated cyanobisarenes on the basis of an interaction of the cyanoarene radical anion with fluorinated substrates activated to aromatic nucleophilic substitution.
Synthesis of highly substituted fluorenones via metal-free TBHP-promoted oxidative cyclization of 2-(aminomethyl)biphenyls. Application to the total synthesis of nobilone
Bracher, Franz,Jourjine, Ilya A. P.,Krau?, Jürgen,Zeisel, Lukas
supporting information, p. 2668 - 2679 (2021/11/30)
Highly substituted fluorenones are readily prepared in mostly fair to good yields via metal- and additive-free TBHP-promoted cross-dehydrogenative coupling (CDC) of readily accessible N-methyl-2-(aminomethyl)biphenyls and 2-(aminomethyl)biphenyls. This methodology is compatible with numerous functional groups (methoxy, cyano, nitro, chloro, and SEM and TBS-protective groups for phenols) and was further utilized in the first total synthesis of the natural product nobilone.
Radical Anions of Aromatic Carbonitriles as Reagents for Arylation of Fluorinated Benzonitriles
Panteleeva, Elena V.,Peshkov, Roman Yu.,Rybalova, Tatyana V.,Tretyakov, Evgeny V.,Wang, Chunyan
, p. 963 - 972 (2021/08/24)
The first example of phenylation of fluorobenzonitriles with the sodium salt of a benzonitrile radical anion in liquid ammonia is presented. The reaction regioselectivity corresponds to the ortho- and para-fluorine atom substitution in fluorobenzonitrile with the phenyl moiety of the benzonitrile radical anion and affords 2- and 4-cyanobiphenyls in 40-90% yields. 3-Methoxybenzonitrile as well as 1-cyanonaphthalene radical anions were also successfully subjected to this interaction forming 3′-methoxycyanobiphenyls and (1-naphthyl)benzonitriles, respectively. The radical anion acts as an ipso-C-nucleophile with consequent loss of the cyano group. The revealed new type of radical anion reactivity opens up the prospect of developing a general approach to fluorinated cyanobisarenes on the basis of an interaction of the cyanoarene radical anion with fluorinated substrates activated to aromatic nucleophilic substitution.
Novel N-biphenyl-2-ylmethyl 2-methoxyphenylpiperazinylalkanamides as 5-HT7R antagonists for the treatment of depression
Kim, Youngjae,Tae, Jinsung,Lee, Kangho,Rhim, Hyewhon,Choo, Il Han,Cho, Heeyeong,Park, Woo-Kyu,Keum, Gyochang,Choo, Hyunah
, p. 4587 - 4596 (2014/10/15)
5-HT7 receptor (5-HT7R) is a promising target for the treatment of depression and neuropathic pain. 5-HT7R antagonists exhibited antidepressant effects, while the agonists produced strong anti-hyperalgesic effects. In our efforts to discover selective 5-HT 7R antagonists or agonists, N-biphenylylmethyl 2- methoxyphenylpiperazinylalkanamides 1 were designed, synthesized, and biologically evaluated against 5-HT7R. Among the synthesized compounds, N-2′-chlorobiphenylylmethyl 2- methoxyphenylpiperazinylpentanamide 1-8 showed the best binding affinity with a Ki value of 8.69 nM and it was verified as a novel antagonist according to functional assays. The compound 1-8 was very selective over 5-HT1DR, 5-HT2AR, 5-HT3R, 5-HT5AR and 5-HT6R and moderately selective over 5-HT1AR, 5-HT1BR and 5-HT2CR. The novel 5-HT7R antagonist 1-8 exhibited an antidepressant effect at a dose of 25 mg/kg in the forced swimming test in mice and showed a U-shaped dose-response curve which typically appears in 5-HT7R antagonists such as SB-269970 and lurasidone.
Novel syntheses of fluorenones via nitrile-directed palladium-catalyzed C-H and dual C-H bond activation
Wan, Jung-Chih,Huang, Jun-Min,Jhan, Yu-Huei,Hsieh, Jen-Chieh
, p. 2742 - 2745 (2013/07/19)
Novel procedures for the [Pd]/[Ag]/TFA system catalyzed cascade reactions of nitrile directed remote C-H and dual C-H bond activation with insertion of nitrile were developed, which afforded variously polysubstituted fluorenones in moderate to good yields with tolerance of a wide variety of substrates.
A mild robust generic protocol for the Suzuki reaction using an air stable catalyst
Moseley, Jonathan D.,Murray, Paul M.,Turp, Edward R.,Tyler, Simon N.G.,Burn, Ross T.
experimental part, p. 6010 - 6017 (2012/09/21)
A mild but robust procedure has been developed as a first pass generic protocol for the Suzuki-Miyaura reaction. The protocol employs an air stable palladium pre-catalyst at low loading (1 mol %) in aqueous solvent mixtures at moderate temperature using potassium carbonate as base. Under these mild conditions, most aryl bromides will react with sterically and electronically demanding aryl boronic acids to give complete conversion to the product biphenyls in less than 1 h. Aryl chlorides are also fully converted in most cases either under identical conditions in 8-24 h, or in 2 h at elevated temperature. A further advantage of these mild conditions of moderate temperature, weak base and benign solvent is that sensitive functional groups and structural motifs are well tolerated. In addition, the lipophilic biphenyl products are readily isolated after a simple work-up procedure. These generic conditions are ideal for proof of transformation, and as the starting point for development and optimization of a specific process. The discovery and fine-tuning of this generic protocol will be presented, supported extensively by examples to illustrate its scope and utility.
A base-free, one-pot diazotization/cross-coupling of anilines with arylboronic acids
Mo, Fanyang,Qiu, Di,Jiang, Yubo,Zhang, Yan,Wang, Jianbo
scheme or table, p. 518 - 522 (2011/02/28)
Pd-catalyzed one-pot diazotization/cross-coupling is realized for the synthesis of biaryls directly from anilines and arylboronic acids.
Microwave-assisted Negishi and Kumada cross-coupling reactions of aryl chlorides
Walla, Peter,Kappe, C. Oliver
, p. 564 - 565 (2007/10/03)
Rapid Pd or Ni-catalyzed microwave-accelerated Negishi and Kumada cross-coupling reactions of aryl chlorides in solution and on solid phase are reported.
