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由 D-樟脑磺酸-氯化铋催化的用 N-卤代琥珀酰亚胺(NXS)对芳香化合物进行卤化反应

Halogenation of aromatic compounds with -halosuccinimides (NXS) catalysed by D-camphorsulfonic acid-BiCl.

作者信息

Tanemura Kiyoshi

机构信息

Chemical Laboratory, School of Life Dentistry at Niigata, Nippon Dental University, Hamaura-cho, Niigata 951-8580, Japan.

出版信息

Org Biomol Chem. 2024 Jun 26;22(25):5105-5111. doi: 10.1039/d4ob00837e.

Abstract

Aromatic bromination catalysed by 0.5-10 mol% of D-camphorsulfonic acid-BiCl3 with -bromosuccinimides (NBS) was carried out in MeCN under air conditions, and the procedure was extended to the reactions with -chlorosuccinimides (NCS) and -iodosuccinimides (NIS). The halogenation of some drugs and natural products was also attempted. One-pot bromination/Suzuki-Miyaura cross-coupling and bromination/Sonogashira coupling reactions were achieved without the removal of the solvent.

摘要

在空气条件下,以0.5 - 10 mol%的D - 樟脑磺酸 - BiCl₃催化,与N - 溴代琥珀酰亚胺(NBS)进行芳族溴化反应,该反应在乙腈中进行,并且该方法扩展到了与N - 氯代琥珀酰亚胺(NCS)和N - 碘代琥珀酰亚胺(NIS)的反应。还尝试了对一些药物和天然产物进行卤化反应。在不除去溶剂的情况下实现了一锅法溴化/铃木 - 宫浦交叉偶联反应和溴化/索尼加什ira偶联反应。

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