Nanonickel‐Catalyzed Suzuki–Miyaura Cross‐Couplings in Water

Handa, Sachin; Slack, Eric D.; Lipshutz, Bruce H.

doi:10.1002/anie.201505136

Cited by 105 publications

(48 citation statements)

References 30 publications

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“…The product was collected as a yellow solid (0.0728 g, 71.9 % yield). C 26 [Zn(2O 2 )Cl 2 ]: ZnCl 2 (0.0222 g, 0.163 mmol) was dissolved in a 2-propanol/methanol (2:1) mixture (2 mL). In a separate flask, 2O 2 (0.0743 g, 0.165 mmol) was dissolved in warm 2-propanol (5 mL).…”

Section: Methodsmentioning

confidence: 99%

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Late Transition Metal Compounds with 1,1′‐Bis(phosphino)ferrocene Ligands

et al. 2016

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Section: Methodsmentioning

confidence: 99%

“…The resulting orange product was collected (0.0646 g, 50.8 % yield). C 26 [Zn(4S)Cl 2 ]: ZnCl 2 (0.0100 g, 0.0730 mmol) and 4S (0.0400 g, 0.0730 mmol) were placed in a flask. Toluene (20 mL) was added, and the reaction mixture was heated under reflux overnight.…”

Section: Methodsmentioning

confidence: 99%

Late Transition Metal Compounds with 1,1′‐Bis(phosphino)ferrocene Ligands

et al. 2016

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“…From the perspective of green chemistry, the development of the aqueous media Suzuki-Miyaura reaction [38][39][40] and Tsuji-Trost reaction 41,42) is a very attractive field, as water is an environmentally benign solvent.…”

Section: -18)mentioning

confidence: 99%

“…36,37) These cross-coupling reactions have been widely used in the synthesis of a variety of fine chemicals and pharmaceutical products, as well as in materials science. From the perspective of green chemistry, the development of the aqueous media Suzuki-Miyaura reaction [38][39][40] and Tsuji-Trost reaction 41,42) is a very attractive field, as water is an environmentally benign solvent.…”

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confidence: 99%

Synthesis of Dendrimers with a Bidentate Phosphine Core Ligand Having Carboxy Groups at the Peripheral Layer and Their Application to Aqueous Media Cross-Coupling Reactions

Fujita

Hattori

2016

CHEMICAL & PHARMACEUTICAL BULLETIN

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We prepared a series of dendrimers with a bidentate phosphine core ligand having carboxy groups at the peripheral layer. By employing the corresponding water-soluble dendritic phosphine-palladium complex as a catalyst, the aqueous media Suzuki-Miyaura reaction and Tsuji-Trost reaction proceeded to provide the corresponding cross-coupling product.Key words dendrimer; phosphine; catalyst With the many environmental challenges faced by the world today, organic reactions that can be conducted in water without the use of harmful organic solvents have been a subject of increasing interest. As a potential solvent, water is not only non-toxic and non-flammable solvent, but also cheap and readily available.1-4) Accordingly, various water-soluble ligands have been synthesized in order to carry out organic reactions in purely aqueous reaction media, and the corresponding water-soluble organometallic catalyst has been applied to aqueous media organic syntheses. [5][6][7][8][9] Dendrimers are fascinating molecules due to the unique physical and chemical properties resulting from their welldefined hyperbranched frameworks.10-14) Metallodendrimers with a functional or catalytic site at their core have received considerable attention, because their solubility and physical properties can be altered by peripheral modification. 15-18)For example, by the introduction of hydrophilic groups to the peripheral layer of a hydrophobic dendron, water-soluble dendritic unimolecular micelles can be prepared.19-28) Some water-soluble dendrimers have been used as catalysts for aqueous media organic syntheses by our group 19,26,27) and by others. 28) We have synthesized a series of dendrimers with a phosphine core ligand having carboxy groups at the peripheral layer 1Gn[CO 2 H] (n=0-2); these are monodentate phosphine ligands, as shown in Fig. 1. 19,27) By employing the corresponding water-soluble 1Gn[CO 2 K]-palladium complex as a catalyst, an aqueous media Suzuki-Miyaura reaction was carried out smoothly, and thus a hydrophobic dendron was effective as a reaction field in the case of aqueous media organic syntheses. 19,27,29,30) We wish to report herein the synthesis of a series of dendrimers with a bidentate phosphine core ligand having carboxy groups at the peripheral layer 2Gn[CO 2 H] (n=0-2), [31][32][33][34][35] as shown in Fig. 1, and an aqueous media Suzuki-Miyaura reaction and Tsuji-Trost reaction catalyzed by the corresponding water-soluble dendritic phosphine 2Gn[CO 2 K]-palladium complex. The Suzuki-Miyaura reaction and Tsuji-Trost reaction have become one of the most powerful cross-coupling methods.36,37) These cross-coupling reactions have been widely used in the synthesis of a variety of fine chemicals and pharmaceutical products, as well as in materials science. From the perspective of green chemistry, the development of the aqueous media Suzuki-Miyaura reaction [38][39][40] and Tsuji-Trost reaction 41,42) is a very attractive field, as water is an environmentally benign solvent.* To whom correspondence should be addressed. e-...

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“…Generally, water offers several "green chemistry" benefits as a solvent in organic transformations, including high efficiency, lower cost, ease of process, green and environmental protection [3,4]. Recently, there are many reports of clean transformations in water medium [5][6][7][8][9][10][11][12][13][14][15][16][17][18][19], such as coupling reactions [20][21][22][23][24][25][26][27][28][29][30], cyclizations [31][32][33][34], Michael additions [35][36][37][38][39], and condensations [40,41]. Additionally, H2O also participates in organic reactions as a nucleophile [42,43] to provide various kinds of functional compounds such as imidazo [1,2-a]pyridines [44], amino acid salts [45], α-amino ketones [46], and 1,3-oxazinan-2-ones [47]…”

Section: Introductionmentioning

confidence: 99%