92-06-8Relevant articles and documents
Single electron transfer reductive cleavage of the aryl-nitrogen bond in phenyl-substituted dimethylanilines
Azzena,Dessanti,Melloni,Pisano
, p. 8291 - 8293 (1999)
By treatment with Li metal in THF at room temperature the three isomeric N,N-dimethylaminobiphenyls and N,N-dimethyl-2,6-diphenylaniline underwent 100% regioselective reductive cleavage of the aryl-N bond, affording biphenyl and meta-terphenyl, respectively, in various yields.
A straightforward synthesis of 4,5-dihalofunctionalized imidazol-2-ylidene/imidazolyl-metal complexes from trihaloimidazolium salts/imidazoles: Structure and catalytic studies
Avinash, Iruthayaraj,Gupta, Vivek,Karthik, Vedhagiri,Anantharaman, Ganapathi
, p. 104 - 114 (2017)
Backbone dihalofunctionalized imidazol-2-ylidene/imidazolyl-metal complexes (5?13) of group–10 metal ions were synthesized through a proficient and single step oxidative addition method using 2,4,5-trihaloimidazolium salts or imidazoles respectively. The donor property of 4,5-diiodofunctionalized imidazol-2-ylidene was described for the first time. The catalytic activity of palladium complexes containing imidazol-2-ylidene (6 and 7)/imidazolyl (10 and 11) groups towards Suzuki-Miyaura coupling reaction of aryl bromides was evaluated and compared with its unsubstituted counterpart. Besides, the investigation of reaction pathway in catalysis was carried out.
Nickel(II) benzimidazolin-2-ylidene complexes with thioether-functionalized side chains as catalysts for Suzuki-Miyaura cross-coupling
Bernhammer, Jan C.,Huynh, Han Vinh
, p. 5845 - 5851 (2014)
Four bis(benzimidazolin-2-ylidene) nickel(II) complexes featuring thioether moieties in the side chain have been synthesized by reactions of the respective benzimidazolium salts with nickel(II) acetate in molten tetrabutylammonium bromide as an ionic liqu
Suzuki cross-coupling of hexachlorobenzene promoted by the Buchwald ligands
Burukin, A. S.,Vasil’ev, A. A.,Zhdankina, G. M.,Zlotin, S. G.
, p. 169 - 172 (2022/02/17)
The study of cross-coupling between hexachlorobenzene and phenylboronic acid comprised five Buchwald ligands, from which 2-dicyclohexylphosphino-2′-(dimethylamino)biphenyl (DavePHOS) provided the best conversion. When excess of phenylboronic acid was used, a mixture of isomeric tri-, tetra- and pentaphenyl-substituted derivatives in the ～10:70:20 ratio was obtained, along with minor amounts of hydrodechlorination products.
Buchwald ligand-assisted Suzuki cross-coupling of polychlorobenzenes
Burukin, Alexander S.,Vasil'ev, Andrei A.,Zhdankina, Galina M.,Zlotin, Sergei G.
, p. 400 - 402 (2021/06/07)
Screening of four Buchwald ligands for the cross-coupling of isomeric di-, tri- and tetrachlorobenzenes with arylboronic acids revealed that good yields of exhaustive substitution can be best provided by 2-dicyclohexylphosphino-2′-(dimethylamino) biphenyl (DavePHOS).
PRODUCTION METHOD OF COUPLING COMPOUND
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Paragraph 0069-0070, (2021/05/05)
PROBLEM TO BE SOLVED: To provide a production method of a coupling compound due to a cross-coupling reaction that uses a novel reaction substrate. SOLUTION: A production method of a coupling compound characterized by producing a compound (C) from a compound (A) and a compound (B) according to a coupling reaction represented by the following formula (1). As a reaction substrate of a cross-coupling reaction, by using a compound having a -SF5 group, which is excellent in safety and has no problem of toxicity of a byproduct, various kinds of coupling compounds may be produced at a high yield. (In the formula (1), R1 and R2 represent independently an arbitrary monovalent atomic group, Z represents a leaving group, and M represents a transition metal catalyst.) SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT
Tris-NHC-propagated self-supported polymer-based Pd catalysts for heterogeneous C-H functionalization
Choudhury, Joyanta,Dutta, Tapas Kumar,Mandal, Tanmoy,Mohanty, Sunit
supporting information, p. 10182 - 10185 (2021/10/12)
Three-dimensionally propagated imidazolium-containing mesoporous coordination polymer and organic polymer-based platforms were successfully exploited to develop single-site heterogenized Pd-NHC catalysts for oxidative arene/heteroarene C-H functionalization reactions. The catalysts were efficient in directed arene halogenation, and nondirected arene and heteroarene arylation reactions. High catalytic activity, excellent heterogeneity and recyclability were offered by these systems making them promising candidates in the area of heterogeneous C-H functionalization, where efficient catalysts are still scarce.
Copper-catalyzed meta-selective arylation of phenol derivatives: An easy access to m-aryl phenols
Maraswami, Manikantha,Hirao, Hajime,Loh, Teck-Peng
, p. 2302 - 2309 (2021/02/20)
Achieving selective meta-functionalization of phenols is a significant challenge. Accessing such compounds generally needs elevated temperature or incorporation of complex templates. Here, we report a general approach to achieve meta-arylated phenols with a simple and common directing group. This coppercatalyzed protocol proceeds with complete meta-selectivity and tolerates a variety of functional groups in both coupling partners. Computational studies have revealed that the reaction proceeded via a Heck-like pathway.
New Nickel-Based Catalytic System with Pincer Pyrrole-Functionalized N-Heterocyclic Carbene as Ligand for Suzuki-Miyaura Cross-Coupling Reactions
Guo, Zhifo,Lei, Xiangyang
supporting information, (2021/09/11)
A new catalytic system with Ni(NO3)2·6H2O as the catalyst and a pincer pyrrole-functionalized N-heterocyclic carbene as the ligand was employed in the Suzuki-Miyaura cross-coupling reactions of aryl iodides with arylboronic acids. With 5 mol% catalyst, the catalytic reactions proceeded at 160 °C, giving coupling products in isolated yields of up to 94% in short reaction times (1-4 h). The system worked efficiently with aryl iodides bearing electron-donating or electron-withdrawing groups and arylboronic acids with electron-donating groups. Steric effects were observed for both aryl iodides and arylboronic acids. It is proposed that the reactions underwent a Ni(I)/Ni(III) catalytic cycle.
Facile Synthesis of Pd Nanoparticles Incorporated into Ultrathin Crystalline g-C3N4with Enhanced Photocatalytic Performance
Cao, Changyan,Huang, Yan,Jiang, Mengying,Li, Jun,Peng, Li,Song, Weiguo,Yang, Shuliang
, p. 7526 - 7532 (2020/11/18)
Driving chemical reactions by use of sunlight is of great importance for a sustainable future. Pd-based catalysts are commonly employed in thermal catalysis for various chemical reactions such as hydrogenation and coupling reactions. However, very few reports were related to Pd for photocatalytic coupling reactions. In this work, a facile method was developed to synthesize ultra-small Pd nanoparticles anchored on ultrathin crystalline graphitic carbon nitride (g-C3N4) for photocatalysis. Monodisperse Pd nanoparticles with a diameter of about 3 nm were dispersed on ultrathin crystalline g-C3N4 uniformly. The prepared Pd/g-C3N4 catalyst could take the advantages of the unique properties of ultra-small Pd nanoparticles and ultrathin crystalline g-C3N4 and thus exhibited markedly enhanced photocatalytic performance toward Suzuki-Miyaura coupling reaction under visible light irradiation. The preparing method could also be extended to the synthesis of Ru/g-C3N4, Pt/g-C3N4, and Ag/g-C3N4.
