Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 7, Issue -, Pages 1671-1679Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.7.197
Keywords
aminoxylation; flow chemistry; heterogeneous catalysis; packed-bed microreactor; proline/thiourea catalysis
Categories
Funding
- NSF [CHE-0809261]
- NDSEG
- Corning Glass
- Pfizer
- FSU
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Herein, we demonstrate that a homogeneous catalyst can be prepared continuously via reaction with a packed-bed of a catalyst precursor. Specifically, we perform continuous proline catalyzed alpha-aminoxylations using a packed-bed of L-proline. The system relies on a multistep sequence in which an aldehyde and thiourea additive are passed through a column of solid proline, presumably forming a soluble oxazolidinone intermediate. This transports a catalytic amount of proline from the packed-bed into the reactor coil for subsequent combination with a solution of nitrosobenzene, affording the desired optically active alpha-aminooxy alcohol after reduction. To our knowledge, this is the first example in which a homogeneous catalyst is produced continuously using a packed-bed. We predict that the method will not only be useful for other L-proline catalyzed reactions, but we also foresee that it could be used to produce other catalytic species in flow.
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