Palladium Supported on Silk Fibroin for Suzuki–Miyaura Cross‐Coupling Reactions

Rizzo, Giorgio; Albano, Gianluigi; Presti, Marco Lo; Milella, Antonella; Omenetto, Fiorenzo G.; Farinola, Gianluca M.

doi:10.1002/ejoc.202001120

Cited by 27 publications

(35 citation statements)

References 75 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…13 4-methyl-1,1'-biphenyl (4 b): [32] White solid; Yield: 76 %; m.p 49-50°C; 1 H NMR (400 MHz, CDCl 3 ) δ 7.50 (d, J = 7.8 Hz, 2H), 7.36 (d, J = 7.9 Hz, 2H), 7.31-7.27 (m, 1H), 7.24 (t, J = 7.4 Hz, 2H), 7.04 (d, J = 7.9 Hz, 2H), 2.29 (s, 3H). 13 methoxy-1,1'-biphenyl (4 c): [33] White solid; Yield: 90 %; m.p 88-90°C; 1 H NMR (400 MHz, CDCl 3 ) δ 7.50 (d, J = 7.8 Hz, 2H), 7.31-7.21 (m, 3H), 7.14 (t, J = 7.88 Hz, 1H), 7.09-7.06 (m, 2H), 6.85-6.82 (m, 1H), 3.78 (s, 3H). 13 methoxy-1,1'-biphenyl (4 d): [32] White solid; Yield: 90 %; m.p 86-90°C; 1 H NMR (400 MHz, CDCl 3 ) δ 7.50 (d, J = 7.76 Hz, 2H), 7.37 (d, J = 8.72 Hz, 2H), 7.3-7.21 (m, 4H), 6.78 (d, J = 8.72 Hz, 1H), 3.77 (s, 3H).…”

Section: Methodsmentioning

confidence: 99%

“…[1,1'-biphenyl]-2-ol (4 e): [33] White solid; Yield: 72 %; m.p 56-58°C; 1 H NMR (500 MHz, CDCl 3 ) δ 7.51 (d, J = 7.88 Hz, 2H), 7.32 (d, J = 7.96 Hz, 1H), 7.29 (d, J = 7.04 Hz, 1H), 7.25-7.22 (m, 2H), 7.18 (t, J = 7.8 Hz, 1H), 7.03 (d, J = 8.12 Hz, 1H), 6.87 (t, J = 7.86 Hz, 1H) 5.67 (bs, 1H). 13 [1,1'-biphenyl]-4-ol (4 f): [32] White solid; Yield: 78 %; m.p 164-165°C; 1 H NMR (400 MHz, CDCl 3 ) δ 7.49 (d, J = 7.7 Hz, 2H), 7.32 (d, J = 8.5 Hz, 2H), 7.28 (d, J = 7.0 Hz, 1H), 7.23 (t, J = 7.4 Hz, 2H), 6.71 (d, J = 8.5 Hz, 2H), 5.42 (bs, 1H).…”

Section: -mentioning

confidence: 99%

“…[1,1'-biphenyl]-4-amine (4 g): [33] White solid; Yield: 76 %; m.p 52-54°C; 1 H NMR (400 MHz, CDCl 3 ) δ 7.50 (d, J = 7.8 Hz, 3H), 7.28 (d, J = 6.9 Hz, 1H), 7.23 (t, J = 7.04 Hz, 4H), 6.55 (d, J = 8.24 Hz, 1H), 3.65 (bs, 2H). 13 [34] Brown solid; Yield: 50 %; m.p 36-38°C; nitro-1,1'-biphenyl (4 i): [32] Yellow needle crystal; Yield: 52 %; m.p 114-115°C; 1 H NMR (400 MHz, CDCl 3 ) δ 8.02 (d, J = 7.9 Hz, 1H), 7.83 (d, J = 8.1 Hz, 1H), 7.48 (d, J = 7.9 Hz, 2H), 7.30-720 (m, 5H).…”

Section: -mentioning

confidence: 99%

See 2 more Smart Citations

Chroman‐4‐one‐Based Amino Bidentate Ligand: An Efficient Ligand for Suzuki‐Miyaura and Mizoroki‐Heck Coupling Reactions in Aqueous Medium

Khan

Parveen

2021

Eur J Org Chem

View full text Add to dashboard Cite

A new family of phosphine-free Amino-chroman-4-one ((Z)-2ethoxy-3-((phenylamino)methylene)chroman-4-one) bidentate ligands ware successfully synthesised and characterised. The bidentate ligand act as efficient catalyst with combination of Pd (II) salt in the CÀ C bond formation and exhibited excellent performance in the Suzuki-Miyaura and Mizoroki-Heck coupling reaction. A broad range of substrates, including heterocyclic, flavones, Isatin and sterically hindered coupling partner, were well tolerated under the optimized reaction conditions. Metal complex and all the intermediates were formed in the catalytic cycle were characterized by mass spectrometry to support the reaction mechanism.

show abstract

Section: Methodsmentioning

confidence: 99%

Section: -mentioning

confidence: 99%

Section: -mentioning

confidence: 99%

See 1 more Smart Citation

Chroman‐4‐one‐Based Amino Bidentate Ligand: An Efficient Ligand for Suzuki‐Miyaura and Mizoroki‐Heck Coupling Reactions in Aqueous Medium

Khan

Parveen

2021

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

“…The palladium content in the resulting solution was determined by ICP-OES analysis and was found to be 0.8 w/w% of the initial Pd (i.e., 1.7 10 −3 mg). This very low value will prompt us to carry out further experiments, such as recycling of the catalyst and Maitlis hot filtration tests [107,108], to evaluate the mechanism (homogeneous or heterogeneous) of the Pd/Smopex ® -234 catalyst in the cyclocarbonylative Sonogashira reaction. 1 The reactions were performed with tosylamide 6 or 7 (2 mmol) and iodobenzene 2a (2.5 mmol), in Et3N (3 mL) and toluene (2 mL), under CO atmosphere (20 atm), at 100 °C.…”

Section: Synthesis and Morphology Of The Catalystsmentioning

confidence: 99%

Palladium Nanoparticles Supported on Smopex-234® as Valuable Catalysts for the Synthesis of Heterocycles

2021

Self Cite

View full text Add to dashboard Cite

Supported catalysts are important tools for developing green-economy-based processes. Palladium nanoparticles (NPs) that are immobilized on two fibers developed as metal scavengers (i.e., Smopex®-234 and Smopex®-111, 1% w/w) have been prepared and tested in copper-free cyclocarbonylative Sonogashira reactions. Their catalytic activity has been compared with that of a homogeneous catalyst (i.e., PdCl2(PPh3)2). Pd/Smopex®-234 showed high activity and selectivity in the synthesis of functionalized heterocycles, such as phthalans and isochromans, even when working with a very low amount of palladium (0.2–0.5 mol%). The extension of Pd/Smopex®-234 promoted cyclocarbonylative reactions to propargyl and homopropargyl amides afforded the corresponding isoindoline and dihydrobenzazepine derivatives. A preliminary test on Pd NPs leaching into the solution (1.7 × 10−3 mg) seems to indicate that, at the end of the reaction, almost all of the active metal is present on the fiber surface.

show abstract

“…It can be processed from aqueous solutions and converted into a variety of versatile systems ( Qi et al, 2017 ; Huang et al, 2018 ; Guo et al, 2020 ), such as hydrogels sponges, foams, solid matrices, ultra-resistant, optically transparent and flexible films among others. Moreover, doping with various organic and inorganic dopants opens up the way to a wide variety of applications ranging from supported catalysts ( Rizzo et al, 2020a ) to environmentally sustainable devices for photonics, electronics, and optoelectronics ( Tao et al, 2012 ; Zhu et al, 2016 ). In fact, SF exhibits a moderate fluorescence (it can be excited at 277 nm and emits light at 345 nm) ( Georgakoudi et al, 2007 ) that has been ascribed to the aromatic moieties of Tryptophan and Tyrosine, commonly used, together with Phenylalanine, as fluorescent probes to study the structure of proteins.…”

Section: Introductionmentioning

confidence: 99%

Bombyx mori Silk Fibroin Regeneration in Solution of Lanthanide Ions: A Systematic Investigation

Rizzo

Presti

Giannini

et al. 2021

Front. Bioeng. Biotechnol.

Self Cite

View full text Add to dashboard Cite

Silk Fibroin (SF) obtained from Bombyx mori is a very attractive biopolymer that can be useful for many technological applications, from optoelectronics and photonics to biomedicine. It can be processed from aqueous solutions to obtain many scaffolds. SF dissolution is possible only with the mediation of chaotropic salts that disrupt the secondary structure of the protein. As a consequence, recovered materials have disordered structures. In a previous paper, it was shown that, by modifying the standard Ajisawa’s method by using a lanthanide salt, CeCl3, as the chaotropic agent, it is possible to regenerate SF as a fibrous material with a very ordered structure, similar to that of the pristine fiber, and doped with Ce+3 ions. Since SF exhibits a moderate fluorescence which can be enhanced by the incorporation of organic molecules, ions and nanoparticles, the possibility of doping it with lanthanide ions could be an appealing approach for the development of new photonic systems. Here, a systematic investigation of the behavior of degummed SF in the presence of all lanthanide ions, Ln+3, is reported. It has been found that all lanthanide chlorides are chaotropic salts for solubilizing SF. Ln+3 ions at the beginning and the end of the series (La+3, Pr+3, Er+3, Tm+3, Yb+3, Lu+3) favor the reprecipitation of fibrous SF as already found for Ce+3. In most cases, the obtained fiber preserves the morphological and structural features of the pristine SF. With the exception of SF treated with La+3, Tm+3, and Lu+3, for all the fibers re-precipitated a concentration of Ln+3 between 0.2 and 0.4% at was measured, comparable to that measured for Ce+3-doped SF.

show abstract

Palladium Supported on Silk Fibroin for Suzuki–Miyaura Cross‐Coupling Reactions

Cited by 27 publications

References 75 publications

Chroman‐4‐one‐Based Amino Bidentate Ligand: An Efficient Ligand for Suzuki‐Miyaura and Mizoroki‐Heck Coupling Reactions in Aqueous Medium

Chroman‐4‐one‐Based Amino Bidentate Ligand: An Efficient Ligand for Suzuki‐Miyaura and Mizoroki‐Heck Coupling Reactions in Aqueous Medium

Palladium Nanoparticles Supported on Smopex-234® as Valuable Catalysts for the Synthesis of Heterocycles

Bombyx mori Silk Fibroin Regeneration in Solution of Lanthanide Ions: A Systematic Investigation

Contact Info

Product

Resources

About