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Catalysts for Suzuki–Miyaura Coupling Reaction

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A special issue of Catalysts (ISSN 2073-4344). This special issue belongs to the section "Catalysis in Organic and Polymer Chemistry".

Deadline for manuscript submissions: closed (28 February 2019) | Viewed by 59480

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Prof. Dr. Christophe Len

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1. Sorbonne Universités, Université de Technologie de Compiegne, F-60203 Compiegne, France
2. Chimie ParisTech, CNRS, PSL University, F-75005 Paris, France
Interests: fine chemistry from natural substances: carbohydrates, cyclodextrins, nucleosides, lipids; chemistry and processes for the sustainable development; organic chemistry in green solvents; homogeneous, heterogeneous, and micellar catalysis; continuous flow applied to organic chemistry; organic chemistry under microwave activation
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Dear Colleagues,

Among the most popular processes in organic chemistry for carbon–carbon (C-C) bond formation, the Suzuki–Miyaura cross coupling reaction permits to produce various industrial chemicals for pharmaceutical, drug, agrochemical, and polymer companies. Recently, promising alternatives to improve and expand the scope of this process are being made based on renewable resources, energy efficiency, atom economy, less-hazardous chemical steps, safer (least toxic) solvents, auxiliaries and alternative technologies.

The aim of this Special Issue is to cover promising recent research and novel trends in the field of Suzuki–Miyaura, carbon–carbon, bond-forming processes using various homogeneous and heterogeneous catalysts under mild experimental conditions compatible with many functional groups. The transformations may use: (i) fossil or bio-based compounds/reagents either in a sequential way or in a one-pot combined synthesis; (ii) mono- or biphasic system either in a fossil solvent or in eco-friendly media (e.g., water, ionic liquids, deep eutectic, critical fluids, etc.); and (iii) conventional batch chemistry or new ambitious technologies using flow chemistry, microwaves, microreactors, nanocatalysts, and, more remarkably, novel combinations of these technologies. Different aspects of Suzuki–Miyaura cross coupling reaction, such as supported or unsupported catalysts, with or without ligands, coupling of non-activated substrates, catalyst recycling and mechanisms would also be of great interest.

Prof. Dr. Christophe Len
Guest Editor

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Keywords

Suzuki–Miyaura
Cross-coupling
Homogeneous catalyst
Heterogeneous catalyst
Metal nanoparticles
Metal complex
Alternative technologies

Published Papers (14 papers)

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Editorial

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3 pages, 142 KiB

Open AccessEditorial

Catalysts for Suzuki–Miyaura Coupling Reaction

by Christophe Len

Catalysts 2020, 10(1), 50; https://doi.org/10.3390/catal10010050 - 01 Jan 2020

Cited by 4 | Viewed by 2458

Abstract

Among the main reactions in organic chemistry, the Suzuki–Miyaura cross-coupling reaction catalyzed by a homogeneous or heterogeneous palladium complex is undoubtedly the most important [...] Full article

(This article belongs to the Special Issue Catalysts for Suzuki–Miyaura Coupling Reaction)

Research

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14 pages, 4980 KiB

Open AccessArticle

One-Pot Synthesized Pd@N-Doped Graphene: An Efficient Catalyst for Suzuki–Miyaura Couplings

by Mufsir Kuniyil, J. V. Shanmukha Kumar, Syed Farooq Adil, Mohammed Rafi Shaik, Mujeeb Khan, Mohamed E. Assal, Mohammed Rafiq H. Siddiqui and Abdulrahman Al-Warthan

Catalysts 2019, 9(5), 469; https://doi.org/10.3390/catal9050469 - 21 May 2019

Cited by 25 | Viewed by 3954

Abstract

Nitrogen-doped graphene (NDG)-palladium (Pd)-based nanocatalysts (NDG@Pd) can be potentially applied as an efficient catalyst for the preparation of biaryls in a Suzuki–Miyaura coupling reaction. Herein, we report the one-pot facile synthesis of an NDG@Pd nanocatalyst, wherein the nanocatalyst was prepared by the simultaneous reduction of graphene oxide (GRO) and PdCl₂ in the presence of hydrazine hydrate as a reducing agent, while ammonium hydroxide was used as a source of “N’’ on the surface of graphene. The as-synthesized NDG@Pd nanocatalyst, consisting of smaller-sized, spherical-shaped palladium nanoparticles (Pd-NPs) on the surface of NDG, was characterized by several spectroscopic and microscopic techniques, including high-resolution transmission electron microscopy (HRTEM), X-ray diffraction (XRD), ultraviolet–visible spectroscopy (UV-Vis), Fourier-transform infrared spectroscopy (FT-IR), X-ray photoelectron spectroscopy (XPS), and Brunauer–Emmett–Teller (BET). The nanocatalyst displayed outstanding catalytic activity in the Suzuki–Miyaura cross-coupling reactions of phenyl halides with phenyl boronic acids under facile conditions in water. The catalytic activity of NDG@Pd was found to be a more efficient catalyst when compared to pristine highly reduced graphene oxide (HRG) based Pd nanocatalyst (HRG@Pd). Furthermore, the reusability of the catalyst was also tested by repeatedly performing the same reaction using the recovered catalyst. The N-doped catalyst displayed excellent reusability even after several reactions. Full article

(This article belongs to the Special Issue Catalysts for Suzuki–Miyaura Coupling Reaction)

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14 pages, 3431 KiB

Open AccessArticle

Development of Titanium Dioxide-Supported Pd Catalysts for Ligand-Free Suzuki–Miyaura Coupling of Aryl Chlorides

by Tsuyoshi Yamada, Hayato Masuda, Kwihwan Park, Takumu Tachikawa, Naoya Ito, Tomohiro Ichikawa, Masatoshi Yoshimura, Yukio Takagi, Yoshinari Sawama, Yutaka Ohya and Hironao Sajiki

Catalysts 2019, 9(5), 461; https://doi.org/10.3390/catal9050461 - 19 May 2019

Cited by 13 | Viewed by 4766

Abstract

The catalyst activities of various heterogeneous palladium catalysts supported by anatase-, rutile- and brookite-type titanium oxide for ligand-free Suzuki–Miyaura cross-coupling reactions of aryl chlorides were evaluated. Palladium acetate [Pd(OAc)₂], supported on anatase-type titanium oxide (TiO₂) via acetonitrile solution impregnation process without reduction [Pd/TiO₂ (anatase-type)], demonstrated the highest catalyst activity in comparison to those of other titanium oxide (rutile- or brookite-type) supported Pd(OAc)₂ without reduction and reduced Pd/TiO₂ (anatase-type) [Pd(red)/TiO₂ (anatase-type)]. Various aryl chloride and bromide derivatives were smoothly coupled with arylboronic acids including heteroarylboronic acids in the presence of 5–10 mol% Pd/TiO₂ (anatase-type) without the addition of any ligands. Although the fresh Pd/TiO₂ (anatase-type) catalyst was surprisingly comprised of ca. 1:2 mixture of palladium(II) and palladium(0) species according to X-ray photoelectron spectroscopy (XPS), in spite of no reduction process, significant further increment of palladium(0) species was observed during the Suzuki–Miyaura coupling reaction, and Pd/TiO₂ (anatase-type) was converted into a catalyst, which contained palladium(0) species as the main component [ca. 1:5 mixture of palladium(II) and palladium(0) species]. Therefore, the reduction via the electron donation process to the palladium(II) species may have occurred during the reaction on anatase-type titanium oxide. Full article

(This article belongs to the Special Issue Catalysts for Suzuki–Miyaura Coupling Reaction)

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16 pages, 3032 KiB

Open AccessArticle

Synthesis of the First Resorcin[4]arene-Functionalized Triazolium Salts and Their Use in Suzuki–Miyaura Cross-Coupling Reactions

by David Sémeril, Dominique Matt and Rengan Ramesh

Catalysts 2019, 9(4), 388; https://doi.org/10.3390/catal9040388 - 25 Apr 2019

Cited by 3 | Viewed by 3500

Abstract

Two bulky triazolium salts, namely 1-{4(24),6(10),12(16),18(22)-tetramethylenedioxy- 2,8,14,20-tetrapentylresorcin[4]arene-5-yl}-4-phenyl-3-methyl-1H-1,2,3-triazolium tetrafluoro borate (1) and 1,4-bis{4(24),6(10),12(16),18(22)-tetramethylenedioxy-2,8,14,20-tetrapentyl resorcin[4]arene-5-yl}-3-methyl-1H-1,2,3-triazolium iodide (2), have been synthesized and assessed in the palladium-catalyzed Suzuki–Miyaura cross-coupling of aryl chlorides, with aryl boronic acids. As a general trend, the reaction rates obtained with 1 were significantly higher (up to 5 times) than those observed for 2, this mainly reflected a sterically more accessible metal center in the catalytic intermediates formed with 1. The presence of flexible pentyl chains in these intermediates, which might sterically interact with the metal center, when the latter adopts an exo-orientation with respect to the cavity, were likely responsible for the observed good performance. Full article

(This article belongs to the Special Issue Catalysts for Suzuki–Miyaura Coupling Reaction)

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12 pages, 18069 KiB

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Palladium Nanoparticles Supported on Graphene Oxide as Catalysts for the Synthesis of Diarylketones

by Anna M. Trzeciak, Przemyslaw Wojcik, Radoslaw Lisiecki, Yuriy Gerasymchuk, Wieslaw Strek and Janina Legendziewicz

Catalysts 2019, 9(4), 319; https://doi.org/10.3390/catal9040319 - 01 Apr 2019

Cited by 15 | Viewed by 3741

Abstract

Three palladium catalysts supported on graphene oxide (GO) and on its composite with TiO₂ (GO-TiO₂) were prepared and characterized. The presence of Pd NPs of different diameters (4–89 nm) and size distributions was evidenced by TEM measurements. GO-supported palladium efficiently catalysed the carbonylative coupling of iodobenzenes with aryl boronic acids forming relevant diarylketones at 1 atm CO. The highest activity and recyclability were obtained for Pd/GO-TiO₂. The emission behaviour of Pd/GO and Pd/GO-TiO₂ catalysts indicated structural changes occurring during the catalytic reaction. Full article

(This article belongs to the Special Issue Catalysts for Suzuki–Miyaura Coupling Reaction)

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11 pages, 4281 KiB

Open AccessArticle

Blockage Detection and Diagnosis of Externally Parallelized Monolithic Microreactors

by Osamu Tonomura, Satoshi Taniguchi, Kazuki Nishi, Aiichiro Nagaki, Jun-ichi Yoshida, Katsuyuki Hirose, Norio Ishizuka and Shinji Hasebe

Catalysts 2019, 9(4), 308; https://doi.org/10.3390/catal9040308 - 28 Mar 2019

Cited by 11 | Viewed by 3470

Abstract

To realize stable operation of a microchemical system, it is necessary to develop a process monitoring method that can detect and diagnose blocked microreactors. In this study, a system composed of five monolithic microreactors and a split-and-recombine-type flow distributor (SRFD) was developed for Suzuki–Miyaura coupling. Firstly, the effects of operating conditions on the yield was examined by using a single microreactor. After that, an optimal design problem was formulated to maximize the blockage detection performance by adjusting the channel resistances of the SRFD and the sensor locations in the SRFD under the design constraints. To efficiently solve the problem, a pressure drop compartment model, which is analogous to electrical resistance networks, was used. The optimally designed system was experimentally evaluated from the viewpoint of the capability of continuous operation and the blockage detection and diagnosis performance. The evaluation results show that continuous operation was successfully carried out for one hour, and that the artificially generated blockage of each microreactor was accurately identified. The developed system minimized the process performance degradation due to blockage. Full article

(This article belongs to the Special Issue Catalysts for Suzuki–Miyaura Coupling Reaction)

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24 pages, 12799 KiB

Open AccessArticle

Suzuki–Miyaura Coupling Using Monolithic Pd Reactors and Scaling-Up by Series Connection of the Reactors

by Aiichiro Nagaki, Katsuyuki Hirose, Yuya Moriwaki, Masahiro Takumi, Yusuke Takahashi, Koji Mitamura, Kimihiro Matsukawa, Norio Ishizuka and Jun-ichi Yoshida

Catalysts 2019, 9(3), 300; https://doi.org/10.3390/catal9030300 - 25 Mar 2019

Cited by 17 | Viewed by 4447

Abstract

The space integration of the lithiation of aryl halides, the borylation of aryllithiums, and Suzuki–Miyaura coupling using a Pd catalyst supported by a polymer monolith flow reactor without using an intentionally added base was achieved. To scale up the process, a series connection of the monolith Pd reactor was examined. To suppress the increase in the pressure drop caused by the series connection, a monolith reactor having larger pore sizes was developed by varying the temperature of the monolith preparation. The monolithic Pd reactor having larger pore sizes enabled Suzuki–Miyaura coupling at a higher flow rate because of a lower pressure drop and, therefore, an increase in productivity. The present study indicates that series connection of the reactors with a higher flow rate serves as a good method for increasing the productivity without decreasing the yields. Full article

(This article belongs to the Special Issue Catalysts for Suzuki–Miyaura Coupling Reaction)

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10 pages, 3339 KiB

Open AccessArticle

Palladium Comprising Dicationic Bipyridinium Supported Periodic Mesoporous Organosilica (PMO): Pd@Bipy–PMO as an Efficient Hybrid Catalyst for Suzuki–Miyaura Cross-Coupling Reaction in Water

by Arefeh Ahadi, Sadegh Rostamnia, Paria Panahi, Lee D. Wilson, Qingshan Kong, Zengjian An and Mohammadreza Shokouhimehr

Catalysts 2019, 9(2), 140; https://doi.org/10.3390/catal9020140 - 02 Feb 2019

Cited by 63 | Viewed by 4741

Abstract

In this study, we developed a novel catalysts consisting of periodic mesoporous organosilica functionalized with bipyridinium ionic liquid supported palladium. The physiochemical properties of the hybrid catalyst were investigated using Fourier transform infrared spectroscopy, small angle X–ray powder diffraction, field emission scanning electron microscope, transmission electron microscope, nitrogen adsorption–desorption analyses, and atomic absorption spectroscopy. The stabilized Pd species inside the mesochannels provided good catalytic efficiency for the Suzuki–Miyaura coupling reactions in water. The activity of the designed catalysts retained for several consecutive recycle runs. The stability, recoverability, and reusability of the designed heterogeneous catalyst were also studied under various reaction conditions. Full article

(This article belongs to the Special Issue Catalysts for Suzuki–Miyaura Coupling Reaction)

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11 pages, 1637 KiB

Open AccessCommunication

N-Acylphthalimides: Efficient Acyl Coupling Reagents in Suzuki–Miyaura Cross-Coupling by N–C Cleavage Catalyzed by Pd–PEPPSI Precatalysts

by Md. Mahbubur Rahman, Jonathan Buchspies and Michal Szostak

Catalysts 2019, 9(2), 129; https://doi.org/10.3390/catal9020129 - 01 Feb 2019

Cited by 27 | Viewed by 4557

Abstract

We report a general, highly selective method for Suzuki–Miyaura cross-coupling of N-acylphthalimides via N–C(O) acyl cleavage catalyzed by Pd–PEPPSI-type precatalysts. Of broad synthetic interest, the method introduces N-acylphthalimides as new, bench-stable, highly reactive, twist-controlled, amide-based precursors to acyl-metal intermediates. The reaction delivers functionalized biaryl ketones by acylative Suzuki–Miyaura cross-coupling with readily available boronic acids. Studies demonstrate that cheap, easily prepared, and broadly applicable Pd–PEPPSI-type precatalysts supported by a sterically demanding IPr (1,3-Bis-(2,6-diisopropylphenyl)imidazol-2-ylidene) ancillary ligand provide high yields in this reaction. Preliminary selectivity studies and the effect of Pd–N-heterocyclic carbenes (NHC) complexes with allyl-type throw-away ligands are described. We expect that N-acylphthalimides will find significant use as amide-based acyl coupling reagents and cross-coupling precursors to acyl-metal intermediates. Full article

(This article belongs to the Special Issue Catalysts for Suzuki–Miyaura Coupling Reaction)

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13 pages, 5470 KiB

Open AccessArticle

An Amino-Chain Modified β-cyclodextrin: A Supramolecular Ligand for Pd(OAc)2 Acceleration in Suzuki–Miyaura Coupling Reactions in Water

by Vijay Vilas Shinde, Daham Jeong and Seunho Jung

Catalysts 2019, 9(2), 111; https://doi.org/10.3390/catal9020111 - 23 Jan 2019

Cited by 15 | Viewed by 4736

Abstract

A well-designed and synthesized water-soluble class of β-cyclodextrin supported palladium complex PdLn@Et-β-CD could efficiently validate high catalytic activity and act as a supramolecular platform for phosphine-free Suzuki–Miyaura cross-coupling reactions between arylboronic acid/arylboronic ester and aryl halides in water under mild conditions. The presented novel PdLn@Pr-β-CD complex catalyst was characterized by NMR, XRD, FT-IR, and DSC analysis. Furthermore, the role of the PdLn@Et-β-CD fragment in the reaction mechanism studied by molecular complexation was proposed based on FT-IR, 2D NMR (ROESY) spectroscopy, FE-SEM, and DSC spectroscopic analysis. The important benefits of this technique comprise simple phosphine-free preparation of the palladium catalyst, a wide range of functional-group tolerance, and easy recyclability; this method, furthermore, eschews hazardous reagents or solvents. Full article

(This article belongs to the Special Issue Catalysts for Suzuki–Miyaura Coupling Reaction)

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16 pages, 4510 KiB

Open AccessArticle

Pd/DNA as Highly Active and Recyclable Catalyst of Suzuki–Miyaura Coupling

by M. Mart, W. Tylus and A. M. Trzeciak

Catalysts 2018, 8(11), 552; https://doi.org/10.3390/catal8110552 - 16 Nov 2018

Cited by 16 | Viewed by 4064

Abstract

Pd/DNA catalysts were prepared in a mixed H₂O/EtOH solvent using palladium precursors, Pd(OAc)₂ and PdCl₂, in different dosages and salmon fish sperm DNA. As prepared, the Pd/DNA contained Pd(II) and Pd(0) nanoparticles of various sizes and morphologies, depending on the preparation method. Pd/DNA efficiently catalyzed the Suzuki–Miyaura cross-coupling of various aryl bromides with phenylboronic acids. The catalyst was recovered by simple phase separation and then reused in seven consecutive cycles with a high activity. Full article

(This article belongs to the Special Issue Catalysts for Suzuki–Miyaura Coupling Reaction)

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13 pages, 1757 KiB

Open AccessArticle

Interface-Controlled Pd Nanodot-Au Nanoparticle Colloids for Efficient Visible-Light-Induced Photocatalytic Suzuki-Miyaura Coupling Reaction

by Eunmi Kang, Hyeon Ho Shin and Dong-Kwon Lim

Catalysts 2018, 8(10), 463; https://doi.org/10.3390/catal8100463 - 17 Oct 2018

Cited by 13 | Viewed by 4132

Abstract

Plasmonic nanostructures can be employed for performing photocatalytic reactions with visible-light illumination involving two different possible mechanisms, namely, the near-field enhancement and/or direct hot-electron transfer to the conduction band of an active catalyst. In this study, we demonstrate the significant contribution of a graphene interface layer present between plasmonic nanoparticles and active catalysts (Pd nanodots) in enhancing the photocatalytic efficiency of Pd nanodots through an accelerated electron transfer process. The well-defined Pd-nanodot-modified gold nanoparticles with or without a graphene interface layer were prepared using a wet-chemical synthetic method. The role of the graphene interface was investigated by performing wavelength-dependent reduction studies using potassium hexacyanoferrate (III) in the presence of Pd-nanodot-modified cysteamine-modified AuNPs (Pd-cys-AuNPs), Pd-nanodot-modified graphene oxide (GO)-coated AuNPs (Pd-GO-AuNPs), and Pd-nanodot-modified reduced GO (rGO)-coated AuNPs (Pd-rGO-AuNPs). The fastest rate for the reduction of Fe³⁺ to Fe²⁺ was obtained with Pd-rGO-AuNPs because of the fast electron transfer achieved in the presence of the reduced graphene oxide layer. The highest catalytic activity for the visible-light induced C-C coupling reaction was obtained with Pd-rGO-AuNPs, indicating the role of the graphene interface layer. These results indicate that the design and use of engineered interfaces are of importance to achieve enhanced catalytic activity with plasmonic hybrid nanomaterials. Full article

(This article belongs to the Special Issue Catalysts for Suzuki–Miyaura Coupling Reaction)

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12 pages, 3046 KiB

Open AccessArticle

Novel Magnetically-Recyclable, Nitrogen-Doped Fe₃O₄@Pd NPs for Suzuki–Miyaura Coupling and Their Application in the Synthesis of Crizotinib

by Kai Zheng, Chao Shen, Jun Qiao, Jianying Tong, Jianzhong Jin and Pengfei Zhang

Catalysts 2018, 8(10), 443; https://doi.org/10.3390/catal8100443 - 10 Oct 2018

Cited by 10 | Viewed by 3602

Abstract

Novel magnetically recyclable Fe₃O₄@Pd nanoparticles (NPs) were favorably synthesized by fixing palladium on the surface of nitrogen-doped magnetic nanocomposites. These catalysts were fully characterized by Fourier-transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), transmission electron microscopy (TEM), thermogravimetric analysis (TG), and X-ray photoelectron spectroscopy (XPS). The prepared catalyst exhibited good catalytic activity for Suzuki–Miyaura coupling reactions of aryl or heteroaryl halides (I, Br, Cl) with arylboronic acids. These as-prepared catalysts could be readily isolated from the reaction liquid by an external magnet and reused at least ten times with excellent yields achieved. In addition, using this protocol, the marketed drug crizotinib (anti-tumor) could be easily synthesized. Full article

(This article belongs to the Special Issue Catalysts for Suzuki–Miyaura Coupling Reaction)

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8 pages, 3662 KiB

Open AccessFeature PaperReview

Recent Developments in the Suzuki–Miyaura Reaction Using Nitroarenes as Electrophilic Coupling Reagents

by Lou Rocard and Piétrick Hudhomme

Catalysts 2019, 9(3), 213; https://doi.org/10.3390/catal9030213 - 26 Feb 2019

Cited by 27 | Viewed by 7277

Abstract

Palladium-catalyzed cross-coupling reactions are nowadays essential in organic synthesis for the construction of C–C, C–N, C–O, and other C-heteroatom bonds. The 2010 Nobel Prize in Chemistry to Richard F. Heck, Ei-ichi Negishi, and Akira Suzuki was awarded for the discovery of these reactions. These great advances for organic chemists stimulated intense research efforts worldwide dedicated to studying these reactions. Among them, the Suzuki–Miyaura coupling (SMC) reaction, which usually involves an organoboron reagent and an organic halide or triflate in the presence of a base and a palladium catalyst, has become, in the last few decades, one of the most popular tools for the creation of C–C bonds. In this review, we present recent progress concerning the SMC reaction with the original use of nitroarenes as electrophilic coupling partners reacting with the organoboron reagent. Full article

(This article belongs to the Special Issue Catalysts for Suzuki–Miyaura Coupling Reaction)

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