Visible Light-Catalyzed Benzylic C-H Bond Chlorination by a Combination of Organic Dye (Acr+-Mes) and N-Chlorosuccinimide.,The Journal of Organic Chemistry

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Visible Light-Catalyzed Benzylic C-H Bond Chlorination by a Combination of Organic Dye (Acr+-Mes) and N-Chlorosuccinimide.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-05-20 , DOI: 10.1021/acs.joc.0c01000
Ming Xiang _{1,

2} , Chao Zhou _{1,

2} , Xiu-Long Yang _{1,

2} , Bin Chen _{1,

2} , Chen-Ho Tung _{1,

2} , Li-Zhu Wu _{1,

2}

Affiliation

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^•-Mes.

中文翻译：

通过有机染料（Acr + -Mes）和N-氯代琥珀酰亚胺的组合进行可见光催化的苯甲酰CH键氯化反应。

通过将作为安全氯源的“ N-氯琥珀酰亚胺（NCS）”与作为光催化剂的“ Acr ⁺ -Mes”相结合，我们在可见光照射下成功实现了苄基C–H键氯化。此外，通过加入甲醇钠可以一锅法将苄基氯平稳地转化为苄基醚。这种温和且可扩展的氯化方法可有效地用于多种甲苯衍生物，尤其是对于缺电子的底物。仔细的机理研究表明，NCS提供了一个氢抽象剂“ N-中心的琥珀酰亚胺基”，该基团依赖于Acr ^• -Mes的还原能力来裂解苄基的C–H键。

更新日期：2020-07-17

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