2016
DOI: 10.1556/1846.2016.00021
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Abstract: An integrated process including continuous-flow syntheses directly coupled to product isolation via continuous crystallization is presented. For the synthesis part, Ce 0.495 Sn 0.495 Pd 0.01 O 2-δ was used as heterogeneous catalyst in a custom-made packed-bed reactor (the so-called "Plug and Play" reactor) for continuous Suzuki-Miyaura crosscouplings of various para-and ortho-substituted bromoarenes with phenylboronic acid using environmentally friendly aqueous ethanolic mixtures as reaction solvents. The reac… Show more

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Cited by 16 publications
(21 citation statements)
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“…This is comparable with previously reported Suzuki-Miyaura flow reactors (TOF 10 1 to 10 4 h −1 ) [24,[26][27][28]67], however such systems require high pressures or elevated temperatures. The beneficial preferential separation of iodobenzene reactant and biphenyl product from the phenylboronic acid and reaction solvents in the present study can be ascribed to the selective solubility of the prepared membrane system, Scheme 3.…”
Section: Discussionsupporting
confidence: 90%
See 1 more Smart Citation
“…This is comparable with previously reported Suzuki-Miyaura flow reactors (TOF 10 1 to 10 4 h −1 ) [24,[26][27][28]67], however such systems require high pressures or elevated temperatures. The beneficial preferential separation of iodobenzene reactant and biphenyl product from the phenylboronic acid and reaction solvents in the present study can be ascribed to the selective solubility of the prepared membrane system, Scheme 3.…”
Section: Discussionsupporting
confidence: 90%
“…However, not only are high temperatures and loadings necessary to achieve adequate yields, significant levels of metal leaching are observed. Lower palladium loadings have been reported for other solid support materials (these include metal phosphates [23], metal oxides [24], and organic polymers [25]). Despite such heterogeneous systems displaying reduced palladium leaching compared to conventional Pd/C systems, elevated temperatures or microwave heating are still needed to achieve high product yields.…”
Section: Introductionmentioning
confidence: 89%
“…For the Suzuki-Miyaura cross-coupling, the use of in-house developed Pd-catalysts with the formula Ce 0.99-x Sn x Pd 0.01 O 2-δ is envisaged. Their applicability for cross-couplings of various orthoand para-substituted bromoarenes with phenylboronic acid has already been reported by our group [27,29]. The heterogeneous catalysts also proved to exhibit high functional group tolerance as well as minimal leaching behavior [27,29].…”
Section: Electronic Supplementary Materialsmentioning
confidence: 77%
“…For the second step, the Heck coupling of 3 with 2, an inhouse developed heterogeneous Pd-catalyst 45,53 ‡ (Pdsubstituted cerium-tin-oxide with the molecular formula Sn 0.79 Ce 0.20 Pd 0.01 O 2−δ ) was successfully tested for its activity in the novel solvent system. Full conversion of 3 was reached within 30 min (Fig.…”
Section: Heck Coupling In Batchmentioning
confidence: 99%
“…Furthermore, the combination of both reactions as cascade in flow lower the risks associated to the spontaneous polymerization of the intermediate hydroxystyrene. While conventional flow chemistry, [38][39][40][41][42][43] also including C-C coupling reactions, 39,[44][45][46][47] and continuous biocatalysis [48][49][50] are currently in the focus of many researchers, examples for their successful combination are rare, which can also be attributed by the difficulties to find suitable reaction media. 51 In this work we present a fully integrated two-step flow setup consisting of an enzymatic decarboxylation with a phenolic acid decarboxylase from Bacillus subtilis (BsPAD), followed by a Heck reaction catalyzed by a Pd-substituted Ce-Sn-oxide as shown in Scheme 1.…”
Section: Introductionmentioning
confidence: 99%