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Synfacts 2015; 11(9): 0997
DOI: 10.1055/s-0035-1560139
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Flow Reactors Using Hollow Fibers for Acid, Base, or Chiral Rhodium Catalysis

Contributor(s):
Yasuhiro Uozumi
,
Yoichi M. A. Yamada
,
Takuma Sato
Moschetta EG, Negretti S, Chepiga KM, Brunelli NA, Labreche Y, Feng Y, Rezaei F, Lively RP, Koros WJ, Davies HM. L, * Jones CW. * Georgia Institute for Technology and Emory University, Atlanta, USA
Composite Polymer/Oxide Hollow Fiber Contactors: Versatile and Scalable Flow Reactors for Heterogeneous Catalytic Reactions in Organic Synthesis.

Angew. Chem. Int. Ed. 2015;
54: 6470-6474
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Publication History

Publication Date:
18 August 2015 (online)

 
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Key words

flow chemistry - heterogeneous catalysis - hollow fibers - rhodium

Significance

Flow reaction systems using composite hollow cellulose acetate fibers containing embedded catalysts {ZSM-5 (aluminosilicate MFI zeolite), 3-aminopropyl (APS)-functionalized silica, and the immobilized analogue of Rh2(S-DOSP)4 [DOSP = N-(4-dodecylphenylsulfonyl)prolinato]} were developed for heterogeneous catalytic reactions. The acid-catalyzed hydrolysis of (dimeth­oxymethyl)benzene (1) to benzaldehyde (2) on ZSM-5/fiber, the Knoevenagel condensation of benzaldehyde (2) with malononitrile (3) on APS fiber, and a rhodium-catalyzed enantioselective cyclopropanation on the Rh2(S-DOSP)4 fiber all proceeded efficiently.


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Comment

The catalysts were embedded within the permeable fiber walls (approximately 300–400 µm thick), and the reactants were fed through the bores of the composite hollow fibers. The fiber was surrounded by a sweeping flow of organic solvent that facilitated product collection. The fiber was capped at the end furthest from the inlet to ensure the reactants flowed through the walls and contacted to the catalyst.


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