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N -Arylbenzo[ b ]phenothiazines as Reducing Photoredox Catalysts for Nucleophilic Additions of Alcohols to Styrenes: Shift towards Visible Light

Seyfert, Fabienne; Wagenknecht, Hans-Achim

Abstract:
N-Phenylphenothiazines are an important class of photoredox catalysts because they are synthetically well accessible, they allow the tuning of the optoelectronic properties by different substituents, and they have strong reduction properties for activation of alkenes. One of the major disadvantages of N-phenylphenothiazines, however, is the excitation at 365 nm in the UV-A light range. We synthesized three differently dialkylamino-substituted N-phenylbenzo[b]phenothiazines as alternative photoredox catalysts and applied them for the nucleo­philic addition of alkohols to α-methyl styrene. The additional benzene ring shift the absorbance bathochromically and allows performing the photocatalyses by excitation at 385 nm and 405 nm. This type of photoredox catalysis tolerates other functional groups, as representatively shown for alcohols as substrates with C–C and C–N triple bonds.

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Verlagsausgabe §
DOI: 10.5445/IR/1000129567
Veröffentlicht am 12.02.2021
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Organische Chemie (IOC)
Publikationstyp Zeitschriftenaufsatz
Publikationsjahr 2020
Sprache Englisch
Identifikator ISSN: 0936-5214, 1437-2096
KITopen-ID: 1000129567
Erschienen in Synlett
Verlag Thieme Gruppe
Nachgewiesen in Scopus
Web of Science
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