Recent Developments in the Suzuki-Miyaura Reaction: 2010–2014

Maluenda, Irene; Navarro, Oscar

doi:10.3390/molecules20057528

Cited by 299 publications

(162 citation statements)

References 183 publications

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“…compounds 1a-c) [10], we decided to use these compounds further in the preparation of phosphinoferrocene amidosulfonate donors with varied, electron-rich phosphine substituents, compounds 4a-c (Scheme 1). The synthesis, structural characterization and an evaluation of these compounds as supporting ligands in Pd-catalyzed cyanation of aryl bromides to the corresponding nitriles [11,12] and Suzuki-Miyaura cross-coupling of aryl bromides with arylboronic acids [13][14][15][16][17] performed in aqueous reaction media are reported in this contribution.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structural Characterization and Catalytic Evaluation of Anionic Phosphinoferrocene Amidosulfonate Ligands

et al. 2017

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Triethylammonium salts of phosphinoferrocene amidosulfonates with electron-rich dialkyphosphino substituents, R 2 PfcCONHCH 2 SO 3 (HNEt 3 ) (4a-c), where fc = ferrocene-1,1 -diyl, and R = i-Pr (a), cyclohexyl (Cy; b), and t-butyl (c), were synthesized from the corresponding phosphinocarboxylic acids-borane adducts, R 2 PfcCO 2 H·BH 3 (1a-c), via esters R 2 PfcCO 2 C 6 F 5 ·BH 3 (2a-c) and adducts R 2 PfcCONHCH 2 SO 3 (HNEt 3 )·BH 3 (3a-c). Compound 4b was shown to react with [Pd(µ-Cl)(η-C 3 H 5 )] 2 and AgClO 4 to afford the zwitterionic complex [Pd(η 3 -C 3 H 5 ) (Cy 2 PfcCONHCH 2 SO 3 -κ 2 O,P)] (5b), in which the amidosulfonate ligand coordinates as a chelating donor making use of its phosphine moiety and amide oxygen. The structures of 3b·CH 2 Cl 2 , 4b and 5b·CH 2 Cl 2 were determined by single-crystal X-ray diffraction analysis. Compounds 4a-c and their known diphenylphosphino analogue, Ph 2 PfcCONHCH 2 SO 3 (HNEt 3 ) (4d), were studied as supporting ligands in Pd-catalyzed cyanation of aryl bromides with K 4 [Fe(CN) 6 ] and in Suzuki-Miyaura biaryl cross-coupling performed in aqueous reaction media under mild reaction conditions. In the former reaction, the best results were achieved with a catalyst generated from [PdCl 2 (cod)] (cod = η 2 :η 2 -cycloocta-1,5-diene) and 2 equiv. of the least electron-rich ligand 4d in dioxane-water as a solvent. In contrast, the biaryl coupling was advantageously performed with a catalyst resulting from palladium(II) acetate and ligand 4a (1 equiv.) in the same solvent.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Structural Characterization and Catalytic Evaluation of Anionic Phosphinoferrocene Amidosulfonate Ligands

et al. 2017

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“…After stirring for 20 min, MeOH (10 mL) and NaBH 4 (1.2 mmol) were successively added. After a further 1 h, the reaction was quenched with saturated aqueous NH 4 Cl solution (5 mL), and extracted with EtOAc (3 × 10 mL). The combined organic extracts were washed with brine, dried with magnesium sulfate and concentrated under reduced pressure.…”

Section: General Procedures For Addition/reduction Sequencementioning

confidence: 99%

“…This reaction has become for decades a major methodological tool available to chemists to build molecular architectures especially based on a biaryl scaffold. The biaryl motif can be found in numerous natural products, agrochemicals, drugs, polymers, ligands and thus triggered the attention of the scientific community for a wide range of applications [2][3][4][5][6][7][8][9]. If the formation of a biphenyl motif belongs nowadays to a textbook knowledge, the past decade has witnessed spectacular innovations and improvements such as ligandless transformations [10], supported or nanostructured catalytic systems [11][12][13], performing additives [14,15], neat and/or aqueous conditions [2,13,15], MW activations [10] for example.…”

Section: Introductionmentioning

confidence: 99%

Aziridine- and Azetidine-Pd Catalytic Combinations. Synthesis and Evaluation of the Ligand Ring Size Impact on Suzuki-Miyaura Reaction Issues

et al. 2017

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Abstract:The synthesis of new vicinal diamines based on aziridine and azetidine cores as well as the comparison of their catalytic activities as ligand in the Suzuki-Miyaura coupling reaction are described in this communication. The synthesis of three-and four-membered ring heterocycles substituted by a methylamine pendant arm is detailed from the parent nitrile derivatives. Complexation to palladium under various conditions has been examined affording vicinal diamines or amine-imidate complexes. The efficiency of four new catalytic systems is compared in the preparation of variously substituted biaryls. Aziridine-and azetidine-based catalytic systems allowed Suzuki-Miyaura reactions from aryl halides including chlorides with catalytic loadings until 0.001% at temperatures ranging from 100 • C to r.t. The evolution of the Pd-metallacycle ring strain moving from azetidine to aziridine in combination with a methylamine or an imidate pendant arm impacted the Suzuki-Miyaura reaction issue.

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“…In particular, Suzuki-Miyaura are one of the most widely used reactions for the preparation of biphenyl derivatives [2]. These reactions have been principally carried out using homogeneous catalysts based on simple or sophisticated Pd complexes [2][3][4][5].…”

Section: Introductionmentioning

confidence: 99%

Suzuki-Miyaura C-C Coupling Reactions Catalyzed by Supported Pd Nanoparticles for the Preparation of Fluorinated Biphenyl Derivatives

et al. 2017

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Heterogeneous recyclable catalysts in Suzuki-Miyaura C-C coupling reactions are of great interest in green chemistry as reusable alternatives to homogeneous Pd complexes. Considering the interesting properties of fluorinated compounds for the pharmaceutical industry, as precursors of novel materials, and also as components of liquid crystalline media, this present study describes the preparation of different fluorinated biphenyl derivatives by Suzuki-Miyaura coupling reactions catalyzed by a heterogeneous system (G-COOH-Pd-10) based on Pd nanoparticles supported onto COOH-modified graphene. The catalytic activity of the hybrid material G-COOH-Pd-10 has been tested in Suzuki-Miyaura C-C coupling reactions observing excellent versatility and good conversion rates in the reactions of phenylboronic acid, 4-vinylphenylboronic acid, 4-carboxyphenylboronic acid, and 4-fluorophenylboronic acid with 1-bromo-4-fluorobenzene. In addition, the influence of the arylbromide has been studied by carrying out reactions of 4-fluorophenylboronic acid with 1-bromo-2-fluorobenzene, 1-bromo-3-fluorobenzene, 1-bromo-4-fluorobenzene, 2-bromo-5-fluorotoluene, and 2-bromo-4-fluorotoluene. Finally, catalyst recyclability tests show a good degree of reusability of the system based on G-COOH-Pd-10 as the decrease in catalytic activity after five consecutive catalytic cycles in the reaction of 1-bromo-4-fluorobenzene with 4-florophenylboronic acid at 48 hours of reaction is lower than 8% while in the case of reactions at three hours the recyclability of the systems is much lower.

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Recent Developments in the Suzuki-Miyaura Reaction: 2010–2014

Cited by 299 publications

References 183 publications

Synthesis, Structural Characterization and Catalytic Evaluation of Anionic Phosphinoferrocene Amidosulfonate Ligands

Synthesis, Structural Characterization and Catalytic Evaluation of Anionic Phosphinoferrocene Amidosulfonate Ligands

Aziridine- and Azetidine-Pd Catalytic Combinations. Synthesis and Evaluation of the Ligand Ring Size Impact on Suzuki-Miyaura Reaction Issues

Suzuki-Miyaura C-C Coupling Reactions Catalyzed by Supported Pd Nanoparticles for the Preparation of Fluorinated Biphenyl Derivatives

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