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Complementary Photocatalytic Toolbox: Control of Intramolecular endo-versus exo-trig Cyclizations of α-Phenyl Olefins to Oxaheterocyclic Products

Weick, F. 1; Steuernagel, D. ORCID iD icon 1; Belov, A. 1; Wagenknecht, H.-A. 1
1 Institut für Organische Chemie (IOC), Karlsruher Institut für Technologie (KIT)

Abstract:

The regioselectivity of the intramolecular cyclization of bifunctional α-phenyl alkenes can be controlled simply by the choice of the organic chromophore as the photocatalyst. The central photoredox catalytic reaction in both cases is a nucleophilic addition of the hydroxy function to the olefin function of the substrates. N,N-(4-Diisobutylaminophenyl)phenothiazine catalyzes exo-trig cyclizations, whereas 1,7-dicyanoperylene-3,4,9,10-tetracarboxylic acid bisimides catalyze endo-trig additions to products with anti-Markovnikov regioselectivity. We preliminarily report the photoredox catalytic conversions of 11 representative substrates into 20 oxaheterocycles in order to demonstrate the similarity, but also the complementarity, of these two variants in this photoredox catalytic toolbox.


Verlagsausgabe §
DOI: 10.5445/IR/1000143609
Veröffentlicht am 10.03.2022
Originalveröffentlichung
DOI: 10.1055/s-0040-1719871
Scopus
Zitationen: 2
Web of Science
Zitationen: 2
Dimensions
Zitationen: 2
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Organische Chemie (IOC)
Publikationstyp Zeitschriftenaufsatz
Publikationsjahr 2022
Sprache Englisch
Identifikator ISSN: 0936-5214, 1437-2096
KITopen-ID: 1000143609
Erschienen in Synlett
Verlag Thieme Gruppe
Band 2022
Heft 33
Seiten st-2021-v0312-c
Nachgewiesen in Web of Science
Scopus
Dimensions
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