Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 14, Pages 9080-9087Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c01000
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Funding
- Ministry of Science and Technology of China [2017YFA0206903]
- National Natural Science Foundation of China [21861132004]
- Strategic Priority Research Program of the Chinese Academy of Science [XDB17000000]
- Key Research Program of Frontier Sciences of the Chinese Academy of Science [QYZDY-SSW-JSC029]
- K. C. Wong Education Foundation
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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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