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The Concept of Photozymes: Short Peptides with Photoredox Catalytic Activity for Nucleophilic Additions to α-Phenyl Styrenes

Sack, D.; Wagenknecht, H.-A.

Abstract:

Conventional photoredox catalytic additions of alcohols to olefins require additives, like thiophenol, to promote back electron transfer. The concept of “photozymes” assumes that forward and backward electron transfer steps in a photoredox catalytic cycle are controllable by substrate binding to photocatalytically active peptides. Accordingly, we synthesized a short tripeptide modified with 1,7-dicyano-perylene-3,4 : 9,10-tetracarboxylic acid bisimide as photoredox catalyst. This peptide undergoes an unconventional photoredox catalytic cycle with the radical anion and dianion of the perylene bisimide-peptide as intermediates. The photoredox catalytic reactions with α-phenyl styrenes as substrates require remarkably low catalyst loadings (0.5 mol%) and give the methoxylation products in high yields. The concept of “photozymes” for photoredox catalysis has significant potential for other photocatalytic reactions, in particular with respect to enantioselective photocatalysis.


Verlagsausgabe §
DOI: 10.5445/IR/1000140707
Originalveröffentlichung
DOI: 10.1002/ejoc.202101068
Scopus
Zitationen: 3
Web of Science
Zitationen: 3
Dimensions
Zitationen: 3
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Organische Chemie (IOC)
Publikationstyp Zeitschriftenaufsatz
Publikationsdatum 14.12.2021
Sprache Englisch
Identifikator ISSN: 1434-193X, 0075-4617, 0170-2041, 0365-5490, 0947-3440, 1099-0690, 1434-243X
KITopen-ID: 1000140707
Erschienen in European Journal of Organic Chemistry
Verlag John Wiley and Sons
Band 2021
Heft 46
Seiten 6400-6407
Vorab online veröffentlicht am 28.10.2021
Nachgewiesen in Web of Science
Dimensions
Scopus
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