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Synfacts 2024; 20(09): 0969
DOI: 10.1055/s-0043-1775273
DOI: 10.1055/s-0043-1775273
Organo- and Biocatalysis
Photocalatytic C–H Alkylation Enabled by a Zwitterionic Acridinium Amidate Catalyst
Entgelmeier L.-M,
Mori S,
Sendo S,
Yamaguchi R,
Suzuki R,
Yanai T,
*,
García Mancheño O,
*,
Ohmatsu K,
*,
Ooi T.
*
Nagoya University, Japan
Zwitterionic Acridinium Amidate: A Nitrogen-Centered Radical Catalyst for Photoinduced Direct Hydrogen Atom Transfer.
Angew. Chem. Int. Ed. 2024; e202404890
DOI: 10.1002/anie.202404890.
Zwitterionic Acridinium Amidate: A Nitrogen-Centered Radical Catalyst for Photoinduced Direct Hydrogen Atom Transfer.
Angew. Chem. Int. Ed. 2024; e202404890
DOI: 10.1002/anie.202404890.
Key words
photocatalysis - acridinium amidate - nitrogen-centered radical - C–H alkylation - hydrogen atom transfer
Significance
Ooi, Ohmatsu, García Mancheño, Yanai, and co-workers disclose a photocatalytic alkylation of unactivated C–H bonds using electrophilic olefins. To this end, a zwitterionic acridinium amidate was designed as a direct hydrogen atom transfer catalyst, furnishing the products in good to excellent yields.
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Comment
Mechanistic studies show that hydrogen bonding of the catalyst to HFIP as well as the perpendicular orientation of the 2p orbitals of the acridinium and amidate N-atoms enable the formation of a twisted, catalytically active diradical upon photoexication and intramolecular charge transfer.
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Publication History
Article published online:
16 August 2024
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