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. 2023 Feb 8;8(7):7128-7134.
doi: 10.1021/acsomega.2c08206. eCollection 2023 Feb 21.

Synthesis of α-CF3 Amides via Palladium-Catalyzed Carbonylation of 2-Bromo-3,3,3-trifluoropropene

Xiao Rui Wen  1 , Wen Qing Zhu  1 , Cai Lin Zhang  1 , Hong Li  1 , Jin Zhang  1 , Min Ge Yang  1 , Yong Li Kou  2 , Yu Xia Liu  3 , Yang Li  1
Affiliations

Synthesis of α-CF3 Amides via Palladium-Catalyzed Carbonylation of 2-Bromo-3,3,3-trifluoropropene

Xiao Rui Wen et al. ACS Omega. .

Abstract

Amide compounds are important organic compounds, which play an important role in biomedical chemistry, materials science, life science, and other fields. The synthesis of α-CF3 amides, especially compounds containing 3-(trifluoromethyl)-1,3,4,5-tetrahydro-2H-benzo[b][1,4]diazepine-2-one, has long been a challenge due to the tensile properties and instability of the rings. Here, we report an example of palladium-catalyzed carbonylation of CF3-containing olefin to form α-CF3 acrylamide. By controlling the ligands, we can get different amide compounds as products. This method has good substrate adaptability and functional group tolerance.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1. Palladium-Catalyzed Carbonylation of Anilines
Scheme 2
Scheme 2. Gram-Scale Experiment
Scheme 3
Scheme 3. Reaction Mechanism
See this image and copyright information in PMC

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