2051-61-8Relevant articles and documents
Factorial design evaluation of the Suzuki cross-coupling reaction using a magnetically recoverable palladium catalyst
Guerra, Raíza R.G.,Martins, Felipe C.P.,Lima, Carolina G.S.,Gon?alves, Ricardo H.,Leite, Edson R.,Pereira-Filho, Edenir R.,Schwab, Ricardo S.
, p. 903 - 908 (2017)
A magnetically recoverable catalyst [Fe3O4@SiO2-AEAPTMS-Pd(II)] was prepared, fully characterized and had its catalytic activity evaluated on the Suzuki cross-coupling reaction under microwave irradiation. The reaction conditions for the synthesis of biaryl compounds was optimized in two stages - an initial fractional design 24, in which the parameters reaction time, temperature, solvent and catalyst loading were evaluated, followed by a Doehlert design. The factorial design proved to be a viable approach for obtaining the optimal reaction conditions based on a relatively small number of experiments. Additionally, the biaryl derivatives synthesized by this method were obtained with good to excellent yields (71–96%) and the recovery and reuse of the palladium catalyst was also evaluated.
Palladium-catalyzed C-H ortho arylation of benzoic acids with diaryliodonium salts in water
Wu, Zhiqing,Chen, Si,Hu, Chenxu,Li, Zhengkai,Xiang, Haifeng,Zhou, Xiangge
, p. 2839 - 2842 (2013)
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A comparative Suzuki reaction of aryl halides using a new dimeric orthopalladated complex under conventional and microwave irradiation conditions
Hajipour, Abdol R.,Karami, Kazem,Tavakoli, Ghazal
, p. 401 - 405 (2012)
The cross-coupling reaction between phenylboronic acid and various types of aryl halides (Suzuki reaction) was carried out using a catalytic amount of a new phosphine-based catalyst under microwave irradiation. The reaction conditions were optimized and results showed that, by application of this catalytic system, N-methyl-2-pyrrolidone as the solvent and potassium carbonate as the base, reactions could be completed in a short reaction time with high to excellent yields. Copyright 2012 John Wiley & Sons, Ltd. The Suzuki reaction of aryl halides was carried out using a new catalyst under the optimized conditions. Application of microwave irradiation lead to very good results in a short time. Copyright
Cubical Palladium Nanoparticles on C@Fe3O4 for Nitro reduction, Suzuki-Miyaura Coupling and Sequential Reactions
Kumar, Basuvaraj Suresh,Amali, Arlin Jose,Pitchumani, Kasi
, p. 511 - 519 (2016)
Cubical Pd nanoparticles incorporated magnetically recyclable nanoreactor (Pd cNPs/C@Fe3O4) are found to be efficient catalysts for the hydrogenation or aromatic nitrocompounds, Suzuki-Miyaura coupling and the sequential reaction of [Formula presented] coupling followed by reduction of nitrobiphenyl substrates. A variety of aryl iodides, bromides and chlorides were coupled with phenylboronic acids to form corresponding biaryl products and variety of nitro aromatic compounds was hydrogenated with excellent yield and high TON. The catalytic activity of palladium cubical nanoparticles (Pd cNPs) embedded with excess of {100} surface facets are superior compared to Pd spherical nanoparticles (Pd sNPs) embedded with mixed surface facets. The catalytic efficiency remains unaltered even after five repeated cycles. The observed enhanced catalytic activity is attributed to the high density of low-coordinated Pd {100} atoms present at the surface of the Pd cNPs/C@Fe3O4 catalyst, confirmed by HR-TEM studies. Also, the catalyst is truly heterogeneous, highly stable, does not require any toxic ligands, has wide substrate scope in both nitroreduction and Suzuki-Miyaura coupling reaction along with the ability to catalyse in a sequential manner, magnetically separable from the reaction mixture and can be reused.
Suzuki cross-coupling reaction catalyzed by palladium-supported sepiolite
Shimizu, Ken-Ichi,Kan-No, Toshiki,Kodama, Tatsuya,Hagiwara, Hisahiro,Kitayama, Yoshie
, p. 5653 - 5655 (2002)
Palladium-supported sepiolite clay has effectively catalyzed the Suzuki cross-coupling reaction of phenylboronic acid with aryl halide including less reactive electron-rich aryl bromides.
Direct arylation catalysis with chloro[8-(dimesitylboryl)quinoline-κN]copper(I)
Tamang, Sem Raj,Hoefelmeyer, James D.
, p. 2757 - 2762 (2016)
We report direct arylation of arylhalides with unactivated sp2 C-H bonds in benzene and naphthalene using a copper(I) catalyst featuring an ambiphilic ligand, (quinolin-8-yl)dimesitylborane. Direct arylation could be achieved with 0.2 mol % catalyst and 3 equivalents of base (KO(t-Bu)) at 80 °C to afford TON ≈160-190 over 40 hours.
TBAF-assisted palladium-catalyzed Suzuki reaction in water under the ligand and base-free conditions
Wu, Xiang-Mei,Gu, Yong-Bing
, p. 396 - 400 (2012)
Tetrabutyl ammonium fluoride (abbreviated as TBAF)-assisted palladium-catalyzed Suzuki reaction in neat water has been demonstrated under the ligand and base-free conditions. The cross-coupling of aryl or heteroaryl bromides with arylboronic acids generated the corresponding products in good to excellent yields in the presence of low concentration of palladium acetate in combination with TBAF under air.
The dechlorination of polychlorinated biphenyls by UV-irradiation. VIII. Reactions of 2,3- and 3,4-dichlorobiphenyl in a 2-propanol solution
Nishiwaki,Shinoda,Anda,Hida
, p. 3565 - 3568 (1982)
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Biaryl Coupling of Aryldiazonium Salts and Arylboronic Acids Catalysed by Gold
Medina-Mercado, Ignacio,Porcel, Susana
, (2022/03/15)
A gold-catalysed coupling of aryldiazonium salts with arylboronic acids is described. The reactions proceed in satisfactory yields under irradiation with blue LEDs in the presence of KF and a catalytic amount of ascorbic acid. Notably, 4-nitrobenzendiazonium tetrafluoroborate is sufficiently reactive to undergo the coupling with a variety of arylboronic acids in the absence of aryl radical initiators. The coupling is applicable for electron-donating and electron-withdrawing groups present at the para, ortho, and meta positions of both substrates.
Construction of Bulky Ligand Libraries by Ru(II)-Catalyzed P(III)-Assisted ortho-C-H Secondary Alkylation
Li, Jia-Wei,Li, Ming,Liu, Yue-Jin,Tao, Jun-Yang,Wang, Liang-Neng,Zeng, Ming-Hua
supporting information, p. 11915 - 11925 (2021/09/13)
Modification of commercially available biaryl monophosphine ligands via ruthenium(II)-catalyzed P(III)-directed-catalyzed ortho C-H secondary alkylation is described. The use of highly ring-strained norbornene as a secondary alkylating reagent is the key to this transformation. A series of highly bulky ligands with a norbornyl group were obtained in excellent yields. The modified ligands with secondary alkyl group outperformed common substituted phosphines in the Suzuki-Miyaura cross-coupling reaction at a ppm mole level of Pd catalyst.
Efficient photocatalytic chemoselective and stereoselective C-C bond formation over AuPd@N-rich carbon nitride
Jiang, Heyan,Xu, Jie,Zhang, Sishi,Cheng, Hongmei,Zang, Cuicui,Bian, Fengxia
, p. 219 - 229 (2021/01/28)
Heterogeneous chemoselective or stereoselective C-C coupling reactions remain extremely challenging in traditional organic synthesis. Here, we constructed a AuPd@N-rich carbon nitride (NRCN) photocatalyst through simple ammonia solution heat treatment of carbon nitride and then AuPd NP loading. AuPd@NRCN exhibited extraordinary light color promoted catalytic performance in C-C bond formation under visible light in air. Surprisingly, both high chemoselectivity to unsymmetrical Ullmann biaryl products and satisfactory stereoselectivity to Z-type Heck reaction products could be achieved by changing the light source color. Various substrates exhibited great potential for the economical synthesis of unsymmetrical biaryl products and Z-type olefins. Efficient visible light promoted C-I bond activation accompanied with improved photocatalytic coupling reaction efficiency over AuPd@NRCN was verified firstly by in situ DRIFTS. Considering that the Ullmann cross-coupling reaction is a multi-photon reaction, the improved photocatalytic performance in the Ullmann cross-coupling reaction using a combination of light sources with different colors might be due to the activation of different substrates and/or steps requiring different energies, and the combination of the two energy sources was beneficial for improving the activation efficiency of different substrates and/or steps. The activation of iodobenzene and styrene in the Heck reaction with light was also beneficial to the formation of the stilbene product. The light color promoted chemoselectivity and stereoselectivity are expected to have profound impact on organic synthetic methodology improvement. This journal is
