Ruthenium(II)‐Catalyzed Cross‐Coupling of Benzoyl Formic Acids with Toluenes: Synthesis of 2‐Phenylacetophenones

Herein, we report a direct method to synthesize 2‐phenylacetophenone through a ruthenium(II)‐catalyzed cross‐coupling reaction between acyl and benzyl radical. The various derivatives of 2‐phenylacetophenone were prepared easily in moderate to good yields. These reactions provide a straightforward p...

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Bibliographic Details
Published in:European journal of organic chemistry 2021-06, Vol.2021 (21), p.2955-2961
Main Authors: Yang, Shan, Dai, Chenyang, Chen, Yujie, Jiang, Yaqiqi, Shu, Sai, Huang, Zhibin, Zhao, Yingsheng
Format: Article
Language:English
Subjects:
Cross coupling
Decarboxylation
Dehydrogenation
Functional groups
Ketones
Ruthenium
Ruthenium catalysis
Ruthenium compounds
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Summary:Herein, we report a direct method to synthesize 2‐phenylacetophenone through a ruthenium(II)‐catalyzed cross‐coupling reaction between acyl and benzyl radical. The various derivatives of 2‐phenylacetophenone were prepared easily in moderate to good yields. These reactions provide a straightforward pathway to synthesize a variety of ketones bearing various functional groups. We developed a ruthenium‐catalyzed cross‐coupling of benzoyl formic acids in the presence of toluene to form the important 2‐phenylacetophenones analogues. Additionally, we obtained various substituted 2‐phenylacetophenones in moderate to good yields. Preliminary mechanistic analysis revealed that the reaction proceeded via a free radical pathway, and the ruthenium catalyst played an important role in the decarboxylation reaction.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202100432