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Photocatalytic Synthesis of Acetals and Ketals from Aldehydes and Silylenolethers without the Use of Acids

Steuernagel, Desirée ORCID iD icon 1; Wagenknecht, Hans-Achim 1
1 Institut für Organische Chemie (IOC), Karlsruher Institut für Technologie (KIT)

Abstract:

Acetals and ketals are among the most important protecting groups for carbonyl compounds. A new method for acetalization and ketalization by means of photoredox catalysis has been developed. A biscyanolated perylene bisimide is used as an electron-poor photocatalyst, together with green light (525 nm LED). Silylenolethers derived from aldehydes react efficiently to give acetals in good to excellent yields. A broad substrate range was shown with respect to both the aldehydes and the alcohols. The functional group tolerance is high; in particular, acid- and hydrogen-labile protecting groups are tolerated. Aldehydes can also be directly and selectively converted into the respective acetals. Only ketones must be converted to their silylenolethers before ketalization. This photocatalytic method works without any use of acids or photoacids, and does not need any additives or H-atom transfer reagents. Hence, it broadens the substrate scope and repertoire of photoredox catalysis with respect to carbonyl chemistry.


Verlagsausgabe §
DOI: 10.5445/IR/1000155475
Veröffentlicht am 03.02.2023
Originalveröffentlichung
DOI: 10.1002/chem.202203767
Scopus
Zitationen: 4
Dimensions
Zitationen: 4
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Organische Chemie (IOC)
Publikationstyp Zeitschriftenaufsatz
Publikationsjahr 2022
Sprache Englisch
Identifikator ISSN: 0947-6539, 1521-3765
KITopen-ID: 1000155475
Erschienen in Chemistry – A European Journal
Verlag John Wiley and Sons
Band 29
Heft 13
Seiten Art.-Nr.: e202203767
Vorab online veröffentlicht am 16.12.2022
Schlagwörter photocatalysis, carbonyl compounds, enols, perylene bisimide, photochemistry
Nachgewiesen in Web of Science
Scopus
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