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Multi‐Photocatalyst Cascades: Merging Singlet Oxygen Photooxygenations with Photoredox Catalysis for the Synthesis of Alkaloid Frameworks
Author(s) -
Kalaitzakis Dimitris,
Bosveli Artemis,
Sfakianaki Kalliopi,
Montag Tamsyn,
Vassilikogiannakis Georgios
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202012379
Subject(s) - singlet oxygen , photocatalysis , chemistry , furan , radical , chromophore , photochemistry , intramolecular force , corollary , electron transfer , combinatorial chemistry , singlet state , catalysis , oxygen , organic chemistry , physics , nuclear physics , excited state , mathematics , pure mathematics
The development of photocascades that rapidly transform simple and readily accessible furan substrates into polycyclic alkaloid frameworks or erythrina natural products is described. Each of the sequences developed makes use of photocatalyzed energy transfer processes, which generate singlet oxygen, to set up the substrates for the second photocatalyzed reaction, wherein electron transfer generates carbon‐centered radicals for the cyclizations that give the final complex frameworks. A chemical switch has been developed that can “switch off” one photocatalyst; thus, allowing a second photocatalyst to take over control of the sequence. As a corollary, this strategy represents the first time it has been possible to use multiple photocatalysts in photocascades, and, as such, it expands significantly the reactions that can be included in such cascades and the order in which they can be initiated.