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Photoinduced Site-Selective C(sp3)–H Chlorination of Aliphatic Amides
Organic Letters ( IF 5.2 ) Pub Date : 2020-11-11 , DOI: 10.1021/acs.orglett.0c03297
Yanshuo Zhu 1 , Jingcheng Shi 1 , Wei Yu 1
Affiliation  

Herein, we report a new photochemical method for C(sp3)–H chlorination of amides which employs tert-butyl hypochlorite as the chlorinating agent and a household compact fluorescent lamp as the light source. The reaction proceeds via N-heterocyclic carbene SIPr·HCl-promoted N–H chlorination and subsequent photoinduced Hofmann–Löffler–Freytag chlorine atom transfer. The latter process is facilitated by (diacetoxyiodo)benzene. This protocol exhibits a broad scope and is suitable for site-selective chlorination of methyl hydrogen as well as methylene and methine hydrogen.

中文翻译:

脂肪酰胺的光诱导位点选择性C(sp 3)–H氯化

在此,我们报告了一种新的光化学方法,用于酰胺的C(sp 3)-H氯化反应,该方法采用次氯酸丁酯作为氯化剂,并使用家用紧凑型荧光灯作为光源。反应通过N杂环卡宾SIPr·HCl促进的N–H氯化反应进行,随后进行光诱导的Hofmann–Löffler–Freytag氯原子转移。(二乙酰氧基碘)苯促进了后一种方法。该方案具有广泛的适用范围,适用于甲基氢以及亚甲基和次甲基氢的现场选择性氯化。
更新日期:2020-11-21
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