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Synfacts 2023; 19(01): 0037
DOI: 10.1055/s-0042-1753184
DOI: 10.1055/s-0042-1753184
Metals in Synthesis
Palladium-Catalyzed Cross-Coupling of Aryl Halides with Carboxylic Acids by Photoinduced Reductive Elimination
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
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
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.
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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.
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Publication History
Article published online:
16 December 2022
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