Highly atom-efficient and chemoselective reduction of ketones in the presence of aldehydes using heterogeneous catalysts

Takahashi, Yusuke; Mitsudome, Takato; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi

doi:10.1039/c3gc41322e

Cited by 14 publications

(7 citation statements)

References 22 publications

(5 reference statements)

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“…16 Cation-exchanged clays have been reported to catalyse organic transformations such as the formation of acetal. 17 The acetal formation is a condensation between aldehyde and alcohol. Therefore, it is reasonable to assume that MDC is able to catalyze the nucleosidation which is also a condensation between an aldehyde (sugar) and a nucleophile (pyrimidine).…”

Section: Resultsmentioning

confidence: 99%

A Prebiotic Ribosylation of Pyrimidine Nucleobases Promoted by Metal Cations and Clay Minerals

Chen¹,

Zhao²,

Wang³

2021

Preprint

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We report a prebiotically relevant solution to the N1-ribosylation of pyrimidine nucleobases, a well-known challenge in the RNA World hypothesis. It is found that the presence of metal cations and clay mineral enables the previously unachievable direct ribosylation of uracil, providing by far the highest yield. Spectroscopy and chromatography analyses confirmed the formation of ribosylated uracil. The method can also be extended to the ribosylation of 2-pyrimidinone. These findings are also compatible with the metal-doped-clay model developed by our lab for the unified route of the selection of ribose and subsequent syntheses of nucleotide and RNA.

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Section: Resultsmentioning

confidence: 99%

A Prebiotic Ribosylation of Pyrimidine Nucleobases Promoted by Metal Cations and Clay Minerals

Chen¹,

Zhao²,

Wang³

2021

Preprint

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“…These results demonstrated that Cu 2+ -magadiite represents a durable heterogeneous catalyst for the oxidative coupling of DMP to DPQ. Furthermore, Cu 2+ -magadiite was applied to a continuous flow reactor system [ 53 , 54 ]. Cu 2+ -magadiite (0.8 g) was placed in a tubular stainless-steel reactor, and 2.44 g of DMP dissolved in CHCl 3 /EtOH (500 mL, 4/1 v/v) and O 2 were passed through it, successfully giving 2.20 g of DPQ (92% isolated yield) ( Figure 6 ).…”

Section: Resultsmentioning

confidence: 99%

Selective C–C Coupling Reaction of Dimethylphenol to Tetramethyldiphenoquinone Using Molecular Oxygen Catalyzed by Cu Complexes Immobilized in Nanospaces of Structurally-Ordered Materials

et al. 2015

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Two high-performance Cu catalysts were successfully developed by immobilization of Cu ions in the nanospaces of poly(propylene imine) (PPI) dendrimer and magadiite for the selective C–C coupling of 2,6-dimethylphenol (DMP) to 3,3',5,5'-tetramethyldiphenoquinone (DPQ) with O2 as a green oxidant. The PPI dendrimer encapsulated Cu ions in the internal nanovoids to form adjacent Cu species, which exhibited significantly high catalytic activity for the regioselective coupling reaction of DMP compared to previously reported enzyme and metal complex catalysts. The magadiite-immobilized Cu complex acted as a selective heterogeneous catalyst for the oxidative C–C coupling of DMP to DPQ. This heterogeneous catalyst was recoverable from the reaction mixture by simple filtration, reusable without loss of efficiency, and applicable to a continuous flow reactor system. Detailed characterization using ultraviolet-visible (UV-vis), Fourier transform infrared (FTIR), electronic spin resonance (ESR), and X-ray absorption fine structure (XAFS) spectroscopies and the reaction mechanism investigation revealed that the high catalytic performances of these Cu catalysts were ascribed to the adjacent Cu species generated within the nanospaces of the PPI dendrimer and magadiite.

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“…In 2013 a selective flow reduction of ketones over aldehydes using direct in-line H 2 mixing was reported [ 275 ]. The substrates 252 comprised both aldehyde and ketone functionalities and it was found that, by initial acetalisation of the more reactive aldehyde moiety, the ketone could be selectively hydrogenated, leaving the masked aldehyde intact ( Scheme 60 ).…”

Section: Reviewmentioning

confidence: 99%

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

Gambacorta¹,

Sharley²,

Baxendale³

2021

Beilstein J. Org. Chem.

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Due to their intrinsic physical properties, which includes being able to perform as volatile liquids at room and biological temperatures, fragrance ingredients/intermediates make ideal candidates for continuous-flow manufacturing. This review highlights the potential crossover between a multibillion dollar industry and the flourishing sub-field of flow chemistry evolving within the discipline of organic synthesis. This is illustrated through selected examples of industrially important transformations specific to the fragrances and flavours industry and by highlighting the advantages of conducting these transformations by using a flow approach. This review is designed to be a compendium of techniques and apparatus already published in the chemical and engineering literature which would constitute a known solution or inspiration for commonly encountered procedures in the manufacture of fragrance and flavour chemicals.

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Highly atom-efficient and chemoselective reduction of ketones in the presence of aldehydes using heterogeneous catalysts

Cited by 14 publications

References 22 publications

A Prebiotic Ribosylation of Pyrimidine Nucleobases Promoted by Metal Cations and Clay Minerals

A Prebiotic Ribosylation of Pyrimidine Nucleobases Promoted by Metal Cations and Clay Minerals

Selective C–C Coupling Reaction of Dimethylphenol to Tetramethyldiphenoquinone Using Molecular Oxygen Catalyzed by Cu Complexes Immobilized in Nanospaces of Structurally-Ordered Materials

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

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