Exploiting Poly(ethylene glycol) as a Matrix for Liquid-Phase Organic Synthesis

Sieber, Frank; Wentworth, Paul; Janda, Kim D.

doi:10.3390/50801018

Cited by 15 publications

(6 citation statements)

References 44 publications

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“…Analogously to the case of a PEG-bound carbapalladacycle described above, the anchoring of a biphenylphosphine derivatives belonging to the SPhos family has also been presented [13]. Janda and co-workers [40,41] have reported the successful use of triphenylphosphine bonded to PEG as stoichiometric reagent for the reduction of ozonides and as Wittig reagent. Plenio and co-workers [42,43] have used triphenylphosphine including SPhos derivatives bonded to PEG as palladium ligand for the Sonogoshira and Suzuki coupling.…”

Section: Cooperative Effect Of Solvent and Scaffold To Catalysismentioning

confidence: 97%

Crossing the Borders Between Homogeneous and Heterogeneous Catalysis: Developing Recoverable and Reusable Catalytic Systems

2008

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Section: Cooperative Effect Of Solvent and Scaffold To Catalysismentioning

confidence: 97%

Crossing the Borders Between Homogeneous and Heterogeneous Catalysis: Developing Recoverable and Reusable Catalytic Systems

2008

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“…1v & 2t-2v, [17] 1w & 2w, [18] 1z & 2z, [19] 1ab & 2ab, [20] 1ac & 2ac, [21] 1ad & 2ad, [22] 1af [23] and 2af [24] are known in literature. The esters 3b, 3e, 3l, 3o, 3q, and 3r are known in literature [25] [5-(benzyloxy)-2-bromo-4-methoxyphenyl](phenyl)methanol (1y): To the cooled reaction mixture of O-benzyl(ortho-bromo)isovanillin (500 mg, 1.56 mmol), at 0 C, was added phenyl magnesium bromide [4.67 mmol, (prepared from magnesium (112.1 mg, 4.67 mmol) and bromobenzene (1.11 g, 7.00 mmol) in dry THF (5 mL)] in THF (10 mL) under nitrogen atmosphere.…”

Section: General Procedure-2 [For the Open Air Oxidation Of Alcohols mentioning

confidence: 99%

Simple, Copper(I)-Catalyzed Oxidation of Benzylic/Allylic Alcohols to Carbonyl Compounds: Synthesis of Functionalized Cinnamates in One Pot

Reddy

Mahendar

Satyanarayana

2014

Synthetic Communications

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IR spectra were recorded on a Bruker Tensor 37 (FTIR) spectrophotometer. 1 H NMR spectra were recorded on Bruker Avance 400 (400 MHz) spectrometer at 295 K in CDCl 3 ; chemical shifts (δ in ppm) and coupling constants (J in Hz) are reported in standard fashion with reference to either internal standard tetramethylsilane (TMS) (δ H =0.00 ppm) or CHCl 3 (δ H = 7.25 ppm). 13 C NMR spectra were recorded on Bruker Avance 400 (100 MHz) spectrometer at RT in CDCl 3 ; chemical shifts (δ in ppm) are reported relative to CHCl 3 [δ C = 77.00 ppm (central line of triplet)]. In the 13 C NMR, the nature of carbons (C, CH, CH 2 and CH 3 ) was determined by recording the DEPT-135 spectra, and is given in parentheses and noted as s = singlet (for C), d = doublet (for CH), t = triplet (for CH 2 ) and q = quartet (for CH 3 ). In the 1 H-NMR, the following abbreviations were used throughout: s = singlet, d = doublet, t = triplet, q = quartet, qui = quintet, m = multiplet and br. s = broad singlet. The assignment of signals was confirmed by 1 H, 13 C CPD and DEPT spectra. High-resolution mass spectra (HR-MS) were recorded on an Agilent 6538 UHD Q-TOF using multimode source. All small scale dry reactions were carried out using Schlenk tube technique. Reactions were monitored by TLC on silica gel using a mixture of petroleum ether and ethyl acetate as eluents. Reactions were generally run under an argon or nitrogen atmosphere. Solvents-petroleum ether with a boiling range of 60 to 80 C, ethyl acetate, dichloromethane and diethyl ether-were distilled prior use. Diethyl ether and 1,4dioxane were dried over benzophenone/sodium and DMF was dried over calcium hydride. 1,10phenanthroline and aromatic aldehydes were purchased from local sources and used as received. CuI and K 3 PO 4 were purchased from sigma-Aldrich. Acme's silica gel (60-120 mesh) was used for column chromatography (approximately 20 g per one gram of crude material). General Procedure-1 [For the inert oxidation of alcohols to carbonyl compounds; GP-1(method A)]:In an oven dried Schlenk tube, were added alcohol 1 (69.0-199.5 mg, 0.5 mmol), CuI (10 mol%) and 1,10-Phenanthroline (20 mol%) and K 3 PO 4 (2 mmol) followed by the addition of dioxane (2 mL) at room temperature under a nitrogen atmosphere. The stirred reaction mixture was heated in an oil bath at 80 C for 24-48 h. Progress of the reaction was monitored by TLC till the reaction is completed. Then, the reaction mixture was cooled to room temperature, quenched with aqueous NH 4 Cl solution and then extracted with CH 2 Cl 2 (3  10 mL). The organic layer was washed with saturated NaCl solution, dried (Na 2 SO 4 ), and filtered. Evaporation of the solvent under reduced pressure and purification of the crude material by silica gel column chromatography (petroleum ether/ethyl acetate) furnished the aldehyde/ketone 2 (58-92%).Compounds 1a & 2a, 1c & 2c, [1] 1b & 2b, [2] 1d & 2d, [3] 1e & 2e, [4] 1f-n [5] & 2f, [6] 2g, [7] 2h, [8] 2i, [9] 2j, [10] 2k, [11] 2l, [12] 2m, [13] 2n, [14] 1o & 2o, 1z & 2z, 1ad, 2...

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“…We report in this contribution our results in the preparation of new hydrophilic ionic liquid-phases on which poly(ethyleneglycol) units (PEG) are grafted, using solventless reaction conditions, assisted by focused microwave technology …”

Section: Introductionmentioning

confidence: 99%

Ecofriendly Fast Synthesis of Hydrophilic Poly(ethyleneglycol)-Ionic Liquid Matrices for Liquid-Phase Organic Synthesis.

Fraga-Dubreuil

Famelart

Bazureau

2002

Org. Process Res. Dev.

115

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New, hydrophilic poly(ethyleneglycol)-ionic liquids have been synthesized and investigated, based on 1,3-disubstituted imidazolium cations and fluorinated anions (BF 4-, PF 6-, (CF 3 SO 2) 2 Nor or NTf 2-). A series of typical solvent-free reactions have been safely realized using a focused microwave reactor for the preparation of imidazolium chloride precursors in yields ranging from 73 to 94% followed by quantitative anion metathesis exchanges. The poly(ethyleneglycol)-ionic liquid matrices were also characterized by NMR (1 H, 13 C), mass spectrometry (MS), and their dynamic viscosity was determined at 25°C. These poly(ethyleneglycol)-ionic liquid phases (PEG-ILPs) as task-specific ionic liquids are promising tools for synthetic applications in liquid-phase combinatorial chemistry.

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Exploiting Poly(ethylene glycol) as a Matrix for Liquid-Phase Organic Synthesis

Cited by 15 publications

References 44 publications

Crossing the Borders Between Homogeneous and Heterogeneous Catalysis: Developing Recoverable and Reusable Catalytic Systems

Crossing the Borders Between Homogeneous and Heterogeneous Catalysis: Developing Recoverable and Reusable Catalytic Systems

Simple, Copper(I)-Catalyzed Oxidation of Benzylic/Allylic Alcohols to Carbonyl Compounds: Synthesis of Functionalized Cinnamates in One Pot

Ecofriendly Fast Synthesis of Hydrophilic Poly(ethyleneglycol)-Ionic Liquid Matrices for Liquid-Phase Organic Synthesis.

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