Photoinduced Vitamin-B12-Catalyzed meta-C–H Bromination/Chlorination of Phenol Derivatives Assisted by a U-Shaped Nitrile Template

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-10-15 DOI:10.1021/acs.orglett.4c03339

Weiya Zhang, Xianghui Zhu, Huixin Tong, Hongbo Zhao, Yuying Gu, Wenyi Chu

引用次数: 0

Abstract

A photoinduced vitamin-B₁₂-catalyzed meta-C–H bromination/chlorination of phenol derivatives was established using a nitrile directing template and N-bromosuccinimide (NBS)/N-chlorosuccinimide (NCS) as halogenated reagents, and a series of meta-bromination/chlorination products were obtained in yields of 51 to 80%. This strategy overcame the selectivity problem of phenols, which have difficulty obtaining meta-products through conventional electrophilic reactions. Furthermore, natural product resveratrol and an intermediate of the γ-secretase inhibitor were successfully synthesized, which demonstrates the practicability of this method.

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U 形腈模板辅助光诱导维生素 B12 催化苯酚衍生物的元-C-H 溴化/氯化反应

以腈为导向模板，N-溴琥珀酰亚胺（NBS）/N-氯琥珀酰亚胺（NCS）为卤化试剂，建立了一种光诱导维生素-B12催化的苯酚衍生物元-C-H溴化/氯化反应，并获得了一系列元溴化/氯化产物，收率为51%至80%。这一策略克服了酚类化合物难以通过传统亲电反应获得元产物的选择性问题。此外，还成功合成了天然产物白藜芦醇和γ-分泌酶抑制剂的中间体，证明了该方法的实用性。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.