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Synfacts 2023; 19(01): 0037
DOI: 10.1055/s-0042-1753184
Metals in Synthesis

Palladium-Catalyzed Cross-Coupling of Aryl Halides with Carboxylic Acids by Photoinduced Reductive Elimination

Contributor(s):
Martin Oestreich
,
Hendrik F. T. Klare
,
Nektarios Kranidiotis-Hisatomi
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
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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.


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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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