Quality Control of Methyl 3-phenylpropionate. In 2020.0 J ORG CHEM published article about COUPLING REACTION; HYDROCARBONS; HALOGENATION; ACID; HALIDES; MILD; 9-MESITYL-10-METHYLACRIDINIUM; SUCCINIMIDYL; COMPLEXES; OXIDATION in [Xiang, Ming; Zhou, Chao; Yang, Xiu-Long; Chen, Bin; Tung, Chen-Ho; Wu, Li-Zhu] Chinese Acad Sci, Tech Inst Phys & Chem, Key Lab Photochem Convers & Optoelect Mat, Beijing 100190, Peoples R China; [Xiang, Ming; Zhou, Chao; Yang, Xiu-Long; Chen, Bin; Tung, Chen-Ho; Wu, Li-Zhu] Chinese Acad Sci, Univ Chinese Acad Sci, Beijing 100190, Peoples R China; [Xiang, Ming; Zhou, Chao; Yang, Xiu-Long; Chen, Bin; Tung, Chen-Ho; Wu, Li-Zhu] Univ Chinese Acad Sci, Sch Future Technol, Beijing 100049, Peoples R China in 2020.0, Cited 48.0. The Name is Methyl 3-phenylpropionate. Through research, I have a further understanding and discovery of 103-25-3.
By combining N-chlorosuccinimide (NCS)” as the safe chlorine source with Acr(+)-Mes as the photocatalyst, we successfully achieved benzylic C-H bond chlorination under visible light irradiation. Furthermore, benzylic chlorides could be converted to benzylic ethers smoothly in a one-pot manner by adding sodium methoxide. This mild and scalable chlorination method worked effectively for diverse toluene derivatives, especially for electron-deficient substrates. Careful mechanistic studies supported that NCS provided a hydrogen abstractor N-centered succinimidyl radical, which was responsible for the cleavage of the benzylic C-H bond, relying on the reducing ability of Acr(center dot)-Mes.
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Reference:
Patent; SANOFI; US2011/294788; (2011); A1;,
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