Xantphos‐ligated palladium dithiolates: An unprecedented and convenient catalyst for the carbonylative Suzuki–Miyaura cross‐coupling reaction with high turnover number and turnover frequency

2019 ◽  
Vol 34 (1) ◽  
Author(s):  
Vinayak V. Gaikwad ◽  
Pravin A. Mane ◽  
Sandip Dey ◽  
Bhalchandra M. Bhanage
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Turnover Frequency ◽  
Turnover Number ◽  
High Turnover ◽  
Cross Coupling Reaction

KCC-1 supported palladium nanoparticles as an efficient and sustainable nanocatalyst for carbonylative Suzuki–Miyaura cross-coupling

2016 ◽  
Vol 18 (21) ◽  
pp. 5890-5899 ◽  
Author(s):  
Prashant Gautam ◽  
Mahak Dhiman ◽  
Vivek Polshettiwar ◽  
Bhalchandra M. Bhanage
Keyword(s):  
Palladium Nanoparticles ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Cost Effective ◽  
Turnover Number ◽  
High Turnover ◽  
Cross Coupling Reaction ◽  
Supported Palladium ◽  
Very High

This work reports a cost-effective and sustainable protocol for the carbonylative Suzuki–Miyaura cross-coupling reaction catalyzed by palladium nanoparticles (Pd NPs) supported on fibrous nanosilica (KCC-1) with very high turnover number.

scholarly journals Pd(CH3CN)2Cl2/Pipecolinic Acid as a Highly Efficient Catalytic System for Suzuki-Miyaura Cross-coupling Reaction of Bromoaryl Carboxylic Acids in Water

Catalysts ◽  
2019 ◽  
Vol 9 (1) ◽  
pp. 86 ◽  
Author(s):  
Xiaogang Li ◽  
Wenbin Zhang ◽  
Leiqing Fu ◽  
Mengping Guo
Keyword(s):  
Catalytic System ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Catalytic Performance ◽  
High Turnover ◽  
Mild Conditions ◽  
Highly Efficient ◽  
Cross Coupling Reaction ◽  
Pipecolinic Acid ◽  
Excellent Catalytic Performance

In this study, a convenient and highly efficient catalytic system for the Suzuki-Miyaura coupling reaction was investigated under mild conditions. A combination of Pd(CH3CN)2Cl2 and pipecolinic acid showed excellent catalytic performance and afforded high turnover numbers; turnover numbers were up to 4.9 × 105 for the coupling reaction of 4-bromobenzoic acid and tetraphenylboron sodium. The catalytic system was also effective for the indexes of 4-bromobenzoic acid, and high turnover numbers were obtained.

Iridium-catalyzed allyl–allyl cross-coupling of allylic carbonates with (E)-1,3-diarylpropenes

2015 ◽  
Vol 51 (59) ◽  
pp. 11834-11836 ◽  
Author(s):  
Qianjia Yuan ◽  
Kun Yao ◽  
Delong Liu ◽  
Wanbin Zhang
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
High Turnover ◽  
Cross Coupling Reaction

An efficient Ir-catalyzed allyl–allyl cross-coupling reaction of allylic carbonates with (E)-1,3-diarylpropenes was developed to form linear allylated products, 1,5-dienes, regioselectively in excellent yields and with high turnover numbers (up to 2000 S/Ir).

Dabbling with air-stable organoaluminum species

2006 ◽  
Vol 78 (2) ◽  
pp. 511-518 ◽  
Author(s):  
Kallolmay Biswas ◽  
Alex Chapron ◽  
Thea Cooper ◽  
Paul K. Fraser ◽  
Andrew Novak ◽  
...  
Keyword(s):  
Molecular Modeling ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Amine Group ◽  
Turnover Frequency ◽  
Turnover Number ◽  
High Turnover ◽  
Cross Coupling Reactions ◽  
Molecular Modeling Studies ◽  
Very High

Highly stereoselective 1,2-additions of AlMe3 or its air-stable analog DABCO(AlMe3)2 to aldehydes are realized in the presence of a Ni(acac)2-derived catalyst using phosphoramidite ligands giving sec-alcohols in up to 95 % ee. Very high turnover number (TON) (>1500) and turnover frequency (TOF) (>350 h-1) values can be realized in these reactions. The substrate range, trials of various (DABCO)a(AlR3)b reagents (a = 0.1; b = 1.2; R = Me, Et, Bui), ligands, and molecular modeling studies are used to propose a working model for the catalytic cycle and the origin of the stereoselectivity. The phosphoramidite ligand is proposed to bind the nickel in an η2 manner via the P-donor and one of the C=C aryl bonds of the CHAr amine group. Preliminary studies indicate that DABCO(AlMe3)2 can also be used as a methyl source in Pd-catalyzed cross-coupling reactions of ArX (X = Br, I) species.

scholarly journals Pd Nanocatalyst Adorned on Magnetic Chitosan@N-Heterocyclic Carbene: Eco-Compatible Suzuki Cross-Coupling Reaction

Molecules ◽  
2019 ◽  
Vol 24 (17) ◽  
pp. 3048 ◽  
Author(s):  
Roya Sedghi ◽  
Bahareh Heidari ◽  
Hatef Shahmohamadi ◽  
Pourya Zarshenas ◽  
Rajender S. Varma
Keyword(s):  
Electron Microscopy ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
High Turnover ◽  
General Applicability ◽  
Cross Coupling Reaction ◽  
Covalent Grafting ◽  
Multi Walled Carbon Nanotubes ◽  
Optimum Reaction ◽  
The Fourier Transform

A novel magnetic-functionalized-multi-walled carbon nanotubes@chitosan N-heterocyclic carbene-palladium (M-f-MWCNTs@chitosan-NHC-Pd) nanocatalyst is developed in two steps. The first step entails the fabrication of a three-component cross-linking of chitosan utilizing the Debus–Radziszewski imidazole approach. The second step comprised the covalent grafting of prepared cross-linked chitosan to the outer walls of magnetically functionalized MWCNTs (M-f-MWCNTs) followed by introducing PdCl2 to generate the m-f-MWCNTs@cross-linked chitosan with a novel NHC ligand. The repeated units of the amino group in the chitosan polymer chain provide the synthesis of several imidazole units which also increase the number of Pd linkers thus leading to higher catalyst efficiency. The evaluation of catalytic activity was examined in the expeditious synthesis of biaryl compounds using the Suzuki cross-coupling reaction of various aryl halides and aryl boronic acids; ensuing results show the general applicability of nanocatalyst with superior conversion reaction yields, high turnover frequencies (TOFs) and turnover numbers (TON). Meanwhile, nanocatalyst showed admirable potential in reusability tests, being recycled for five runs without losing significant activities under optimum reaction conditions. The successfully synthesis of catalyst and its characterization was confirmed using the Fourier transform infrared spectrometer (FT-IR), spectrometer transmission electron microscopy (TEM), scanning electron microscopy (SEM), X-ray photo-electron spectroscopy (XPS) and thermogravimetric analysis (TGA).

Ferromagnetic Chain Based on Verdazyl-Nitroxide Diradical

2020 ◽  
Author(s):  
Evgeny Tretyakov ◽  
Svetlana Zhivetyeva ◽  
Pavel Petunin ◽  
Dmitry Gorbunov ◽  
Nina Gritsan ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Ferromagnetic Coupling ◽  
Nitronyl Nitroxide ◽  
Triplet Ground State ◽  
One Dimensional ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
Ferromagnetic Chain ◽  
High Yields

<p>Verdazyl-nitroxide diradicals were synthesized using the palladium-catalyzed cross-coupling reaction of the corresponding iodoverdazyls with a nitronyl nitroxide-2-ide gold(I) complex with high yields (up to 82%). The synthesized diradicals were found to be highly thermally stable and have a singlet (D<i>E</i><sub>ST</sub> » -64 cm<sup>–1</sup>) or triplet ground state (D<i>E</i><sub>ST</sub> ³ 25 and 100 cm<sup>–1</sup>), depending on which canonical hydrocarbon diradical type they belong to. Upon crystallization, triplet diradicals form unique one-dimensional (1D) spin <i>S</i> = 1 chains of organic diradicals with intrachain ferromagnetic coupling of <i>J</i>′/<i>k</i><sub>B</sub> from 3 to 6 K.</p>

An Iron-Based Catalyst Enables The Enantioconvergent Synthesis of Chiral 1,1-Diarylalkanes Through a Suzuki-Miyaura Cross-Coupling Reaction

2020 ◽  
Author(s):  
Chet Tyrol ◽  
Nang Yone ◽  
Connor Gallin ◽  
Jeffery Byers
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Radical Intermediates ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Boronic Esters ◽  
Carbon Centered Radical ◽  
Iron Based ◽  
High Yields

By using an iron-based catalyst, access to enantioenriched 1,1-diarylakanes was enabled through an enantioselective Suzuki-Miyaura crosscoupling reaction. The combination of a chiral cyanobis(oxazoline) ligand framework and 1,3,5-trimethoxybenzene additive were essential to afford high yields and enantioselectivities in cross-coupling reactions between unactivated aryl boronic esters and a variety of benzylic chlorides, including challenging ortho-substituted benzylic chloride substrates. Mechanistic investigations implicate a stereoconvergent pathway involving carbon-centered radical intermediates.

Ni(0)-Catalyzed α-Allylic Alkylation of Regular Ketones with 1,3-Dienes under pH and Redox-neutral Conditions

2019 ◽  
Author(s):  
Tiantian Chen ◽  
Yang Yang ◽  
Liyu Xie ◽  
Haijian Yang ◽  
Guangbin Dong ◽  
...  
Keyword(s):  
Oxidative Addition ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Dual Role ◽  
Allylic Alkylation ◽  
Cross Coupling Reaction ◽  
Neutral Conditions

<p>We report a Ni(0)-catalyzed cross coupling reaction between simple ketones and 1,3-dienes. A variety of a-allylic alkylation products were formed in an 1,2-addition manner with excellent regioselectivity. Water was found to significantly accelerate this transformation. A HO-Ni-H species generated from oxidative addition of Ni(0) to H<sub>2</sub>O is proposed to play a “dual role” in activating both the ketone and the diene substrate.</p>

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