Selectfluor-Mediated Simultaneous Cleavage of C–O and C–C Bonds in α,β-Epoxy Ketones Under Transition-Metal-Free Conditions: A Route to 1,2-Diketones

Wang, Heng; Ren, Shaobo; Zhang, Jian; Zhang, Wei; Liu, Yunkui

doi:10.1021/acs.joc.5b00857

Cited by 27 publications

(11 citation statements)

References 46 publications

(44 reference statements)

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“…Benzil: 1 H NMR (400 MHz, CDCl 3 ): δ = 7.97 (d, J = 7.5 Hz, 2 H), 7.65 (t, J = 7.5 Hz, 2 H), 7.50 (t, J = 7.5 Hz, 4 H) ppm. 13 C NMR (100 MHz): δ = 194.7, 135.0, 133.0, 130.0, 129.1 ppm.…”

Section: Methodsmentioning

confidence: 99%

“…1‐Phenyl‐2‐ p ‐tolylethane‐1,2‐dione: 1 H NMR (400 MHz, CDCl 3 ): δ = 7.97 (d, J = 7.5 Hz, 2 H), 7.87 (d, J = 7.5 Hz, 2 H) 7.65 (t, J = 5.8 Hz, 1 H), 7.51 (t, J = 7.5 Hz, 2 H), 7.31 (d, J = 7.5 Hz, 2 H), 2.44 (s, 3 H) ppm. 13 C NMR (CDCl 3 , 100 MHz): δ = 194.9, 194.5, 146.4, 134.9, 133.2, 130.7, 130.2, 130.0, 129.9, 129.1, 22.1 ppm.…”

Section: Methodsmentioning

confidence: 99%

“…1‐(4‐Chlorophenyl)‐2‐phenylethane‐1,2‐dione: 1 H NMR (400 MHz, CDCl 3 ): δ = 7.98–7.91 (m, 4 H), 7.68 (tt, J = 8, 1.2 Hz, 1 H), 7.55–7.47 (m, 4 H) ppm. 13 C NMR (100 MHz): δ = 194.1, 193.2, 141.7, 135.2, 132.9, 131.5, 131.4, 130.1, 129.6, 129.2 ppm.…”

Section: Methodsmentioning

confidence: 99%

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Oxidative Cleavage of Styrenes Catalyzed by a Pd^II Complex of an 8‐Hydroxyquinolinonate Ligand

et al. 2016

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Synthesis and catalytic activity of palladium complexes of 8-(pyridin-2-ylmethoxy)quinolinone (3) were investigated. Complexation of 3 with [Pd(CH 3 CN) 2 Cl 2 ] gave the dimeric palladium complex [{N,N-(3)PdCl} 2 ] (4). The structure of 4 was characterized by 1 H/ 13 C NMR spectroscopy and mass spectrometry, and further confirmed by X-ray crystallography. Complex [a] 5449 4 acts as a catalyst for oxidative cleavage of C=C bonds, and it catalyzes the hydration of styrenes in an anti-Markovnikov Wacker manner to give terminal aldehydes as the initial product, which then undergo C-C cleavage to yield the corresponding benzaldehydes. Systematic studies of this catalysis were performed.Scheme 2. Tautomers of 8-hydroxycarbostyril and ligand 3. Results and Discussion Preparation of Palladium ComplexesScheme 3 outlines the synthetic approach leading to the desired ligand 3. Compound 1 was prepared according to a literature procedure. [9] Starting from 8-hydroxyquinoline (2), oxidation and acetylation followed by basic hydrolysis provided 1 in 65 % yield of isolated product. Nucleophilic substitution of 2-(bromomethyl)pyridine with 1 under basic conditions in acetonitrile gave 3 in 82 % yield, which was characterized by IR and NMR spectroscopy and mass spectrometry. The carbonyl stretching band at 1682 cm -1 in the IR spectrum clearly demonstrates the existence of amido functionality. The 1 H NMR spectrum of 3 in CDCl 3 shows a downfield signal at δ = 10.02 ppm corresponding to C(O)NH. The 13 C NMR chemical shift of the carbonyl carbon atom at δ = 162.6 ppm is in agreement with Scheme 3. Preparation of ligand 3.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Oxidative Cleavage of Styrenes Catalyzed by a Pd^II Complex of an 8‐Hydroxyquinolinonate Ligand

et al. 2016

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“…Based on literature precedent, catalysts generally categorized into phase transfer catalyst, metal/transition metals and enzyme and protein based catalyst ( Fig. 1) [88][89][90][91][92][93][94][95][96][97][98].…”

Section: Type Of Catalystsmentioning

confidence: 99%

One Pot and Two Pot Synthetic Strategies and Biological Applications of Epoxy-Chalcones

Farooq

Ngaini

2020

Chemistry Africa

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Epoxy chalcone is a heterocyclic molecule and an important precursor for the synthesis of biologically active compounds. This mini-review is elucidating the synthetic strategies of chalcone epoxide via one pot and two pot routes including nature of reactants, nature of catalyst and variety of catalyst to improve yield of desired product, biological applications and advantages and drawbacks of these synthetic strategies. One pot route has wide variety of reactants and efficient one is the condensation of aldehyde and ketone. However, two pot route is consisted of chalcone synthesis preceding to epoxy chalcone. The synthetic routes for the preparation of epoxy chalcone and the usage as a precursor for the synthesis of various organic molecules with biological application is comprehensively discussed. This review is outstanding in organic chemistry and pharmaceutical industries to produce new molecules with various applications. Graphic AbstractO O

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“…Protonation reactions of free-base pyridylporphyrins possessing mixed meso-pyridyl and meso-4-aminophenyl groups were also examined by Wamser and coworkers, with the progress of the reaction being monitored, in this case by both UV/Visible [11] and NMR spectroscopy. [32] An interaction was shown to occur between a meso-aminophenyl group of one porphyrin and a protonated pyridyl group or coreprotonated nitrogen of another porphyrin, but no such interaction was present for the free-base pyridyl porphyrins lacking aminophenyl groups at the other meso-positions of the macrocycle.…”

Section: Introductionmentioning

confidence: 99%

Protonation and Electrochemical Properties of Pyridyl‐ and Sulfonatophenyl‐Substituted Porphyrins in Nonaqueous Media

et al. 2017

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International audienceThe protonation and electrochemical properties of positively charged and negatively charged porphyrins are reported in up to five different nonaqueous solvents. The positively charged porphyrins are represented by mono- and di-pyridyl derivatives having the formula Pyx(PhMe)4-xPM, where P=the dianion of the porphyrin macrocycle, PhMe is a meso-tolyl group, Py a meso-pyridyl group, x=1 or 2, and M=H2, NiII, CuII, ZnII, or CoII. The negatively charged porphyrins are comprised of meso-tetrasulfonato derivatives having the formula [(R)4(TPPS)H2]4−(X+)4, where [(TPPS)H2]4− represents the porphyrin with four SO3− groups on the meso-phenyl substituents of the macrocycle, R=H or PEG (PEG=C7H15O4) and X+=H+ or Na+. Each pyridylporphyrin was shown to undergo an initial protonation of the meso-pyridyl group(s) upon addition of acid to the porphyrin solutions and, in the case of the free-base derivatives, this was followed in a second step by a simultaneous protonation of the two core nitrogen atoms on the macrocycle. Two central nitrogen atoms of the sulfonatophenyl porphyrins are also protonated in a single-step process, and the constants for each protonation reaction of Pyx(PhMe)4-xPM and [(R)4(TPPS)H2]4−(X+)4 were determined through spectral titration with trifluoroacetic acid in DMF, DMSO, CH2Cl2, or PhCN, after which the data were related to solvent properties, the measured redox potentials, and the mechanisms for electroreduction under the same solution conditions

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Selectfluor-Mediated Simultaneous Cleavage of C–O and C–C Bonds in α,β-Epoxy Ketones Under Transition-Metal-Free Conditions: A Route to 1,2-Diketones

Cited by 27 publications

References 46 publications

Oxidative Cleavage of Styrenes Catalyzed by a Pd^II Complex of an 8‐Hydroxyquinolinonate Ligand

Oxidative Cleavage of Styrenes Catalyzed by a Pd^II Complex of an 8‐Hydroxyquinolinonate Ligand

One Pot and Two Pot Synthetic Strategies and Biological Applications of Epoxy-Chalcones

Protonation and Electrochemical Properties of Pyridyl‐ and Sulfonatophenyl‐Substituted Porphyrins in Nonaqueous Media

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Selectfluor-Mediated Simultaneous Cleavage of C–O and C–C Bonds in α,β-Epoxy Ketones Under Transition-Metal-Free Conditions: A Route to 1,2-Diketones

Cited by 27 publications

References 46 publications

Oxidative Cleavage of Styrenes Catalyzed by a PdII Complex of an 8‐Hydroxyquinolinonate Ligand

Oxidative Cleavage of Styrenes Catalyzed by a PdII Complex of an 8‐Hydroxyquinolinonate Ligand

One Pot and Two Pot Synthetic Strategies and Biological Applications of Epoxy-Chalcones

Protonation and Electrochemical Properties of Pyridyl‐ and Sulfonatophenyl‐Substituted Porphyrins in Nonaqueous Media

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Product

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Oxidative Cleavage of Styrenes Catalyzed by a Pd^II Complex of an 8‐Hydroxyquinolinonate Ligand

Oxidative Cleavage of Styrenes Catalyzed by a Pd^II Complex of an 8‐Hydroxyquinolinonate Ligand