Catalysis in Capillaries by Pd Thin Films Using Microwave‐Assisted Continuous‐Flow Organic Synthesis (MACOS)

Shore, Gjergji; Morin, Sylvie; Organ, Michael G.

doi:10.1002/ange.200503600

Cited by 69 publications

(24 citation statements)

References 34 publications

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“…Work by Organ and coworkers has demonstrated, that these Pd-on-glass films (and other metal-coated glass capillaries) can be used for a variety of synthetically important flow chemistry applications in an elevated temperature regime [63–64], including Mizoroki–Heck chemistry [62]. It should be emphasized that our interest in this steel-based immobilized catalytic Pd system was mainly to demonstrate reactor contamination/fouling and not of a preparative nature.…”

Section: Resultsmentioning

confidence: 99%

Unusual behavior in the reactivity of 5-substituted-1H-tetrazoles in a resistively heated microreactor

Gutmann¹,

Glasnov²,

Razzaq³

et al. 2011

Beilstein J. Org. Chem.

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SummaryThe decomposition of 5-benzhydryl-1H-tetrazole in an N-methyl-2-pyrrolidone/acetic acid/water mixture was investigated under a variety of high-temperature reaction conditions. Employing a sealed Pyrex glass vial and batch microwave conditions at 240 °C, the tetrazole is comparatively stable and complete decomposition to diphenylmethane requires more than 8 h. Similar kinetic data were obtained in conductively heated flow devices with either stainless steel or Hastelloy coils in the same temperature region. In contrast, in a flow instrument that utilizes direct electric resistance heating of the reactor coil, tetrazole decomposition was dramatically accelerated with rate constants increased by two orders of magnitude. When 5-benzhydryl-1H-tetrazole was exposed to 220 °C in this type of flow reactor, decomposition to diphenylmethane was complete within 10 min. The mechanism and kinetic parameters of tetrazole decomposition under a variety of reaction conditions were investigated. A number of possible explanations for these highly unusual rate accelerations are presented. In addition, general aspects of reactor degradation, corrosion and contamination effects of importance to continuous flow chemistry are discussed.

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Section: Resultsmentioning

confidence: 99%

Unusual behavior in the reactivity of 5-substituted-1H-tetrazoles in a resistively heated microreactor

Gutmann¹,

Glasnov²,

Razzaq³

et al. 2011

Beilstein J. Org. Chem.

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show abstract

“…[6] After some experimentation it was determined that the most robust and catalytically-active films resulted from a two-step deposition process. [7] First, a very fine layer of densely-packed gold particles was deposited directly on the capillary wall from a diethylene glycol/ AuCl 3 solution.…”

Section: Resultsmentioning

confidence: 99%

Gold‐Film‐Catalysed Hydrosilylation of Alkynes by Microwave‐Assisted, Continuous‐Flow Organic Synthesis (MACOS)

Shore

Organ

2008

Chemistry A European J

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“…Fig. 7,41,42 Fig. The biphenyl yields at the end of the second and third 6 h cycling were slightly reduced to 88.7% and 85.3%, respectively.…”

mentioning

confidence: 94%

“…[12][13][14][15] However, such homogeneous continuous-ow systems raise difficulties in product purication and catalyst recovery. [21][22][23] Besides, the swelling of the polymer supports in organic solvents and chemical instability of metal oxides under harsh conditions further increase the complexity of the heterogeneous catalysts in continuous-ow systems. 9 Catalysts anchored on the surfaces of silica, 16 aluminium oxide, 17,18 and polymer beads 19,20 packed into the continuous-ow column have been reported to benet the separation of catalysts from products and reuse of the catalysts.…”

Section: Introductionmentioning

confidence: 99%

3D graphene/nylon rope as a skeleton for noble metal nanocatalysts for highly efficient heterogeneous continuous-flow reactions

et al. 2015

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Continuous-flow catalytic systems represent a highly efficient approach towards scalable synthesis with features of time and energy saving, easy operation, and improved safety. Herein, we rationally design a novel 3D noble metal/graphene/nylon rope to act as a highly efficient catalyst for continuous-flow organic reactions. We show that different noble metal (Pd, Pt, Au and Ag) nanocatalysts and graphene can be readily assembled with the chemically inert nylon rope by a one-step hydrothermal method.Graphene, acting as the interconnector for noble metal nanoparticles and the nylon rope, increases the flexibility and mechanical strength of rope-like catalysts and improves the catalytic activity and stability of the noble metal species. The large voids within the noble metal/graphene/nylon rope catalysts, under optimized reaction conditions, ensure the sufficient chemical transfer for the continuous-flow system.The high catalytic activity and stability of rope catalysts are demonstrated by the Suzuki-Miyaura crosscoupling reaction (SMC) and 4-nitrophenol reduction reaction. Pd/graphene/nylon rope catalysts show a high turnover number of 965 mol h À1 mol Pd À1, a large productivity of 1385 mg h À1 mg Pd À1 at a flow rate of 70 mL h À1 , and a remarkable stability for continuous-flow SMC reactions. Such a novel minifluidic system integrated with 3D noble metal/graphene/nylon rope catalysts can be extended to many important chemical reactions.

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Catalysis in Capillaries by Pd Thin Films Using Microwave‐Assisted Continuous‐Flow Organic Synthesis (MACOS)

Cited by 69 publications

References 34 publications

Unusual behavior in the reactivity of 5-substituted-1H-tetrazoles in a resistively heated microreactor

Unusual behavior in the reactivity of 5-substituted-1H-tetrazoles in a resistively heated microreactor

Gold‐Film‐Catalysed Hydrosilylation of Alkynes by Microwave‐Assisted, Continuous‐Flow Organic Synthesis (MACOS)

3D graphene/nylon rope as a skeleton for noble metal nanocatalysts for highly efficient heterogeneous continuous-flow reactions

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