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
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.
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.
