Citation: Ying Lv, Bing Wang, Haizhu Yu. Mechanism of the Ir/Pd catalyzed photocarboxylation of aryl halides[J]. Chinese Chemical Letters, ;2021, 32(4): 1403-1406. doi: 10.1016/j.cclet.2020.09.045 shu

Mechanism of the Ir/Pd catalyzed photocarboxylation of aryl halides

Ying Lv ^a ,
Bing Wang ^{b, *,} ,
Haizhu Yu ^{a, *,}

a.
Department of Chemistry and Centre for Atomic Engineering of Advanced Materials, Anhui University, Hefei 230601, China
b.
Department of Chemistry, University of Science and Technology of China, Hefei 230026, China

ice123wb@mail.ustc.edu.cn

yuhaizhu@ahu.edu.cn

Received Date: 18 August 2020
Revised Date: 15 September 2020
Accepted Date: 24 September 2020
Available Online: 25 September 2020

Figures(9)

The recent Ir/Pd co-catalyzed photo carboxylation of aromatic halides with CO₂ has shown high efficiency and excellent functional group tolerance for preparing aromatic carboxylic acids and esters. With the aid of density functional theory (DFT) calculations, the carboxylation starts with two parallel steps, i.e., oxidative addition of aromatic halides on Pd⁰ and reductive quenching of the photocatalyst Ir(ppy)₂(dtbpy)⁺ with amine. Thereafter, a successive oxidation of Pd^Ⅱ with the amine radical (generated by the reaction of cationic radical amine and Cs₂CO₃) and Ir^Ⅱ species occurs to generate Pd⁰, from which the carboxylation occurs easily via a coordination, Pd-C insertion step. The release of the carboxylate product then regenerates the catalyst.
- Carboxylation,
- Pd-catalysis,
- DFT,
- Charge state,
- Mechanism
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