pd催化恶唑、苯并恶唑和苯并咪唑与硝基芳烃的c2 -芳基化反应

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2024-11-29 DOI:10.1002/adsc.202401332

Lin Feng, Haiyan Li, Lei Huang, Jiaxin Yao, Wengui Duan, Lin Yu

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引用次数: 0

摘要

报道了一种通过pd催化硝基芳烃和硝基唑的反硝化芳基化反应制备c2芳基化唑的阶梯经济方法。该方案采用合成的上游硝基芳烃作为芳化试剂，通过C-NO<；sub>2 ；和C-H键的选择性裂解进行。各种硝基芳烃和硝基杂芳烃与恶唑、苯并恶唑和甲基苯并咪唑偶联，产率高达95%。以氟诺卡洛芬的合成为例说明了该方法的实用性。这种策略减少了合成步骤，最大限度地减少了污染，提供了巨大的成本效益和环境效益。此外，相对惰性的C-NO<；sub>2；硝基芳烃中的键可以实现后期官能化或逐步偶联反应，为偶氮的c2 -芳基化提供了一种补充方法。

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Pd-Catalyzed Denitrative C2-Arylation of Oxazoles, Benzoxazoles, and Benzimidazoles with Nitroarenes

A step-economic method for C2-arylated azoles via Pd-catalyzed denitrative arylation of nitroarenes and azoles is reported. This protocol employs synthetically upstream nitroarenes as arylating reagents and proceeds through the selective cleavage of the C–NO2 and C–H bonds. Various nitroarenes and nitroheteroarenes were coupled with oxazoles, benzoxazoles, and methylbenzimidazoles, achieving yields of up to 95%. The method's utility is exemplified by its application in the synthesis of Flunoxaprofen. This strategy reduces synthetic steps and minimizes pollution, offering substantial cost-effectiveness and environmental benefits. Furthermore, the relatively inert C–NO2 bond in nitroarenes enables late-stage functionalization or stepwise coupling reactions, providing a complementary method for C2-arylation of azoles.

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来源期刊

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.