Continuous-Flow Synthesis of Arylthio-Cyclopropyl Carbonyl Compounds.

Autor: Moi D; Department of Chemical and Geological Science, University of Cagliari, S.P. No. 8 Km 0.700, 09042 Monserrato, Italy., Cabua MC; Department of Chemical and Geological Science, University of Cagliari, S.P. No. 8 Km 0.700, 09042 Monserrato, Italy., Velichko V; Department of Chemical and Geological Science, University of Cagliari, S.P. No. 8 Km 0.700, 09042 Monserrato, Italy., Cocco A; Department of Chemical and Geological Science, University of Cagliari, S.P. No. 8 Km 0.700, 09042 Monserrato, Italy., Chiappone A; Department of Chemical and Geological Science, University of Cagliari, S.P. No. 8 Km 0.700, 09042 Monserrato, Italy., Mocci R; Department of Chemical and Geological Science, University of Cagliari, S.P. No. 8 Km 0.700, 09042 Monserrato, Italy., Porcu S; Department of Physics, University of Cagliari, S.P. No. 8 Km 0.700, 09042 Monserrato, Italy., Piras M; Department of Medical Sciences and Public Health, University of Cagliari, 09042 Monserrato, Italy., Bianco S; Department of Applied Science and Technology, Politecnico di Torino, C.so Duca degli Abruzzi 24, 10129 Turin, Italy., Pesciaioli F; Department of Physical and Chemical Sciences, University of L'Aquila, Via Vetoio, 67100 L'Aquila, Italy., Secci F; Department of Chemical and Geological Science, University of Cagliari, S.P. No. 8 Km 0.700, 09042 Monserrato, Italy.
Jazyk: angličtina
Zdroj: Molecules (Basel, Switzerland) [Molecules] 2022 Nov 16; Vol. 27 (22). Date of Electronic Publication: 2022 Nov 16.
DOI: 10.3390/molecules27227943
Abstrakt: The straightforward, continuous-flow synthesis of cyclopropyl carbaldehydes and ketones has been developed starting from 2-hydroxycyclobutanones and aryl thiols. This acid-catalyzed mediated procedure allows access to the multigram and easily scalable synthesis of cyclopropyl adducts under mild conditions, using reusable Amberlyst-35 as a catalyst. The resins, suitably ground and used for filling steel columns, have been characterized via TGA, ATR, SEM and BET analyses to describe the physical-chemical properties of the packed bed and the continuous-flow system in detail. To highlight the synthetic versatility of the arylthiocyclopropyl carbonyl compounds, a series of selective oxidation reactions have been performed to access sulfoxide and sulfone carbaldehyde cyclopropanes, oxiranes and carboxylic acid derivatives.
Databáze: MEDLINE
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