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Electron-transfer-initiated benzoin- and Stetter-like reactions in packed-bed reactors for process intensification
- Source :
- Beilstein Journal of Organic Chemistry, Beilstein Journal of Organic Chemistry, Vol 12, Iss 1, Pp 2719-2730 (2016)
- Publication Year :
- 2016
-
Abstract
- A convenient heterogeneous continuous-flow procedure for the polarity reversal of aromatic α-diketones is presented. Propaedeutic batch experiments have been initially performed to select the optimal supported base capable to initiate the two electron-transfer process from the carbamoyl anion of the N,N-dimethylformamide (DMF) solvent to the α-diketone and generate the corresponding enediolate active species. After having identified the 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine on polystyrene (PS-BEMP) as the suitable base, packed-bed microreactors (pressure-resistant stainless-steel columns) have been fabricated and operated to accomplish the chemoselective synthesis of aroylated α-hydroxy ketones and 2-benzoyl-1,4-diones (benzoin- and Stetter-like products, respectively) with a good level of efficiency and with a long-term stability of the packing material (up to five days).
- Subjects :
- Base (chemistry)
continuos-flow
010402 general chemistry
01 natural sciences
Full Research Paper
lcsh:QD241-441
Electron transfer
chemistry.chemical_compound
lcsh:Organic chemistry
Benzoin
C–C coupling
diketone
electron-transfer
umpolung
Organic chemistry
lcsh:Science
chemistry.chemical_classification
Polarity reversal
Packed bed
010405 organic chemistry
Organic Chemistry
Ambientale
0104 chemical sciences
Solvent
Chemistry
chemistry
Chemical engineering
lcsh:Q
Polystyrene
Microreactor
Subjects
Details
- ISSN :
- 18605397
- Volume :
- 12
- Database :
- OpenAIRE
- Journal :
- Beilstein journal of organic chemistry
- Accession number :
- edsair.doi.dedup.....91ea788d2c4879baa87bf7b52c1b05c8