Harnessing a Continuous-Flow Persulfuric Acid Generator for Direct Oxidative Aldehyde Esterifications.

Autor: Nagy BS; Institute of Chemistry, University of Graz, NAWI Graz, Heinrichstrasse 28, A-8010, Graz, Austria., Fu G; Institute of Chemistry, University of Graz, NAWI Graz, Heinrichstrasse 28, A-8010, Graz, Austria., Hone CA; Institute of Chemistry, University of Graz, NAWI Graz, Heinrichstrasse 28, A-8010, Graz, Austria.; Center for Continuous Flow Synthesis and Processing (CC FLOW), Research Center, Pharmaceutical Engineering GmbH (RCPE), Inffeldgasse 13, A-8010, Graz, Austria., Kappe CO; Institute of Chemistry, University of Graz, NAWI Graz, Heinrichstrasse 28, A-8010, Graz, Austria.; Center for Continuous Flow Synthesis and Processing (CC FLOW), Research Center, Pharmaceutical Engineering GmbH (RCPE), Inffeldgasse 13, A-8010, Graz, Austria., Ötvös SB; Institute of Chemistry, University of Graz, NAWI Graz, Heinrichstrasse 28, A-8010, Graz, Austria.; Center for Continuous Flow Synthesis and Processing (CC FLOW), Research Center, Pharmaceutical Engineering GmbH (RCPE), Inffeldgasse 13, A-8010, Graz, Austria.
Jazyk: angličtina
Zdroj: ChemSusChem [ChemSusChem] 2023 Jan 20; Vol. 16 (2), pp. e202201868. Date of Electronic Publication: 2022 Dec 05.
DOI: 10.1002/cssc.202201868
Abstrakt: Persulfuric acid is a well-known oxidant in various industrial-scale purification procedures. However, due to its tendency toward explosive decomposition, its usefulness in organic synthesis remained largely underexplored. Herein, a continuous in situ persulfuric acid generator was developed and applied for oxidative esterification of aldehydes under flow conditions. Sulfuric acid served as a readily available and benign precursor to form persulfuric acid in situ. By taking advantage of the continuous-flow generator concept, safety hazards were significantly reduced, whilst a robust and effective approach was ensured for direct transformations of aldehydes to valuable esters. The process proved useful for the transformation of diverse aliphatic as well as aromatic aldehydes, while its preparative capability was verified by the multigram-scale synthesis of a pharmaceutically relevant key intermediate. The present flow protocol demonstrates the safe, sustainable, and scalable application of persulfuric acid in a manner that would not be amenable to conventional batch processing.
(© 2022 The Authors. ChemSusChem published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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