Toriumi N,
Inoue T,
Iwasawa N.
*
Tokyo Institute of Technology, Japan
Shining Visible Light on Reductive Elimination: Acridine–Pd-Catalyzed Cross-Coupling of Aryl Halides with Carboxylic Acids.
J. Am. Chem. Soc. 2022;
144: 19592-19602
DOI:
10.1021/jacs.2c09318
Key words
acridines - aryl halides - carboxylic acids - palladium catalysis - photoexcitation
Significance
A palladium-catalyzed cross-coupling of aryl halides with carboxylic acids under visible-light irradiation is disclosed. The reaction affords aryl esters in moderate to good yields. Key to success is the design and use of a non-innocent phosphinoacridine ligand.
Comment
Experimental mechanistic studies revealed that the palladium(II) species undergoes a photoinduced reductive elimination, which is promoted by a metal-to-ligand charge transfer (MLCT) in the excited state.
