Water-soluble salen–Pd complex as an efficient catalyst for Suzuki–Miyaura reaction of sterically hindered substrates in pure water

Liu, Yashuai; Gu, Ning; Liu, Ping; Ma, Xinbin; Liu, Yan; Xie, Jianwei; Dai, Bin

doi:10.1016/j.tet.2015.08.070

Cited by 26 publications

(15 citation statements)

References 74 publications

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“…Compound 6 c : Colorless liquid; 1 H NMR (CDCl 3 , 500 MHz): δ =7.56 (s, 1 H), 7.44 (d, J= 7.5 Hz, 1 H), 7.36–7.29 (m, 5 H), 7.18 (d, J= 7.0 Hz, 1 H), 2.41 ppm (s, 3 H); 13 C NMR (CDCl 3 , 125 MHz): δ =143.2, 139.8, 138.5, 134.6, 129.9, 128.8, 128.6, 127.9, 127.3, 127.1, 125.3, 124.2, 21.5 ppm.…”

Section: Methodsmentioning

confidence: 99%

“…Compound 6 g : White solid; 1 H NMR (CDCl 3 , 500 MHz): δ =7.52 (t, J= 1.5 Hz, 1 H), 7.50–7.47 (m, 2 H), 7.40 (dt, J= 8.0, 1.5 Hz, 1 H), 7.31 (t, J= 8.0 Hz, 1 H), 7.27–7.24 (m, 1 H), 6.98–6.95 (m, 2 H), 3.83 ppm (s, 3 H); 13 C NMR (CDCl 3 , 125 MHz): δ =159.6, 142.7, 134.6, 132.3, 129.9, 128.1, 126.8, 126.6, 124.8, 114.3, 55.3 ppm.…”

Section: Methodsmentioning

confidence: 99%

“…Compound 6 p : White solid; 1 H NMR (CDCl 3 , 500 MHz): δ =7.55 (d, J= 7.5 Hz, 2 H), 7.51 (d, J= 8.5 Hz, 2 H), 7.45–7.40 (m, 4 H), 7.36 ppm (t, J= 7.5 Hz, 1 H); 13 C NMR (CDCl 3 , 125 MHz): δ =140.0, 139.7, 133.4, 128.89, 128.86, 128.4, 127.6, 127.0 ppm.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of N‐Heterocyclic Carbene–Pd^II–2‐Methyl‐4,5‐dihydrooxazole Complexes and Their Application Toward Highly Chemoselective Mono‐Suzuki–Miyaura Coupling of Dichlorobenzenes

Sun

et al. 2018

Asian J Org Chem

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As eries of N-heterocyclic carbene-palladium(II)-2methyl-4,5-dihydrooxazole complexes was synthesized in a one-step process, one of whichf acilitated high chemoselectivity in the mono-Suzuki-Miyaura coupling of dichlorobenzenes. Further transformations of the mono-coupling prod-ucts catalyzed by this complex werea lso investigated, which gave the desired CÀCa nd CÀNc oupling products in excellent yields. The reported methodology allows the conversion of readily available dichlorobenzenes into synthetically useful chlorobiphenyls.Compound 6v: [6] Colorless liquid; 1 HNMR (CDCl 3 ,5 00 MHz): d = 7. 46-7.45 (m, 1H), 7.40-7.36 (m, 1H), 7.30-7.26 (m, 3H), 7.19 (dd, J = 7.5, 1.5 Hz, 1H), 7.03 (t, J = 7.5 Hz, 1H), 6.99 (d, J = 8.5 Hz, 1H), 3.78 ppm (s, 3H); 13 CNMR (CDCl 3 ,1 25 MHz): d = 156.8, 137.8, 133.9, Asian

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Synthesis of N‐Heterocyclic Carbene–Pd^II–2‐Methyl‐4,5‐dihydrooxazole Complexes and Their Application Toward Highly Chemoselective Mono‐Suzuki–Miyaura Coupling of Dichlorobenzenes

Sun

et al. 2018

Asian J Org Chem

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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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ChemInform Abstract: Water‐Soluble Salen—Pd Complex as an Efficient Catalyst for Suzuki—Miyaura Reaction of Sterically Hindered Substrates in Pure Water.

Liu

et al. 2016

ChemInform

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Water-soluble salen–Pd complex as an efficient catalyst for Suzuki–Miyaura reaction of sterically hindered substrates in pure water

Cited by 26 publications

References 74 publications

Synthesis of N‐Heterocyclic Carbene–Pd^II–2‐Methyl‐4,5‐dihydrooxazole Complexes and Their Application Toward Highly Chemoselective Mono‐Suzuki–Miyaura Coupling of Dichlorobenzenes

Synthesis of N‐Heterocyclic Carbene–Pd^II–2‐Methyl‐4,5‐dihydrooxazole Complexes and Their Application Toward Highly Chemoselective Mono‐Suzuki–Miyaura Coupling of Dichlorobenzenes

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

ChemInform Abstract: Water‐Soluble Salen—Pd Complex as an Efficient Catalyst for Suzuki—Miyaura Reaction of Sterically Hindered Substrates in Pure Water.

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Water-soluble salen–Pd complex as an efficient catalyst for Suzuki–Miyaura reaction of sterically hindered substrates in pure water

Cited by 26 publications

References 74 publications

Synthesis of N‐Heterocyclic Carbene–PdII–2‐Methyl‐4,5‐dihydrooxazole Complexes and Their Application Toward Highly Chemoselective Mono‐Suzuki–Miyaura Coupling of Dichlorobenzenes

Synthesis of N‐Heterocyclic Carbene–PdII–2‐Methyl‐4,5‐dihydrooxazole Complexes and Their Application Toward Highly Chemoselective Mono‐Suzuki–Miyaura Coupling of Dichlorobenzenes

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

ChemInform Abstract: Water‐Soluble Salen—Pd Complex as an Efficient Catalyst for Suzuki—Miyaura Reaction of Sterically Hindered Substrates in Pure Water.

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Synthesis of N‐Heterocyclic Carbene–Pd^II–2‐Methyl‐4,5‐dihydrooxazole Complexes and Their Application Toward Highly Chemoselective Mono‐Suzuki–Miyaura Coupling of Dichlorobenzenes

Synthesis of N‐Heterocyclic Carbene–Pd^II–2‐Methyl‐4,5‐dihydrooxazole Complexes and Their Application Toward Highly Chemoselective Mono‐Suzuki–Miyaura Coupling of Dichlorobenzenes