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

Benjamin List; Wencke Leinung

doi:10.1055/s-0043-1775273

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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
DOI: 10.1002/anie.202404890

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Abstract
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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.

Publication History

Article published online:
16 August 2024

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