由异氰基乙酰胺和芳基偶氮砜制备芳基偶氮噁唑的路易斯酸促进/可见光驱动双重方法

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2024-10-31 DOI:10.1002/adsc.202401079

Enzo Delalande, Lorenzo Di Terlizzi, Camilla Russo, Carmine Volpe, Stefano Protti, mariateresa giustiniano

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引用次数: 0

摘要

尽管芳基偶氮砜已被广泛用作芳基化剂，但其在重氮化反应中的应用以前仅限于富电子烯烃，如苯乙烯和硅烷基烯醇醚。在此，我们优化了一种单锅合成方案，以芳基偶氮砜和异氰基乙酰胺为起点，在 Sm(OTf)3 作为路易斯酸的存在下，通过选择性多米诺闭环/芳基偶氮化序列获得恶唑基偶氮化合物。令人满意的底物范围和官能团耐受性，以及在间歇和连续流动条件下的放大反应，为这类杂芳基偶氮化合物提供了一种宝贵的方法。

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Dual Lewis Acid Promoted/Visible Light Driven Preparation of Aryl Diazenyl Oxazoles from Isocyanoacetamides and Arylazo Sulfones

While arylazo sulfones have been widely applied as arylating agents, their exploitation for diazenylation reactions has been previously limited to electron-rich alkenes such as styrenes and silyl enol ethers. Herein we optimized a synthetic one-pot protocol to access oxazolyl azo compounds via a selective domino ring-closing/aryldiazenylation sequence by starting from arylazo sulfones and isocyanoacetamides in the presence of Sm(OTf)3 as the Lewis acid. The satisfactory substrate scope and functional group tolerance, along with scale-up reaction both in batch and under continuous flow conditions provide a valuable approach to such a class of heteroaryl azo compounds.

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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.