Synfacts 2024; 20(09): 0969
DOI: 10.1055/s-0043-1775273
Organo- and Biocatalysis

Photocalatytic C–H Alkylation Enabled by a Zwitterionic Acridinium Amidate Catalyst

Contributor(s):
Benjamin List
,
Wencke Leinung
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
 

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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