Efficient synthesis of chlorinated Dihydronaphthalene derivatives using N,N-diisopropylformamide-POCl3 as a Vilsmeier reagent

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters Pub Date : 2025-06-27 DOI:10.1016/j.tetlet.2025.155726

Dinghao Li , Junwei Li , Yumeng Zhang, Fang-Lin Zhang

引用次数: 0

Abstract

A newly developed chlorinating reagent (N,N-diisopropylformamide-POCl₃ complex) and metal halide (ZnCl₂) synergistic reaction system was reported for the efficient chlorination of polysubstituted 1-tetralones. This protocol facilitates the reaction to proceed under mild conditions with this in situ formed Vilsmeier reagent, and a broad substrate scope could be compatible. 28 examples were successfully converted to the corresponding chlorodihydronaphthalenes in moderate to good yields, meanwhile significantly suppressing the formation of halogenated enal byproducts. The simplicity, high efficiency and wide substrate compatibility enable this new method to be a promising alternative for the synthesis of halogenated aryl olefins and drug molecules.

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以N，N-二异丙基甲酰胺- pocl3为维斯迈试剂高效合成氯化二氢萘衍生物

报道了一种新型氯化试剂（N，N-二异丙基甲酰胺- pocl3配合物）与金属卤化物（ZnCl2）协同反应体系的高效氯化反应。该方案有助于在温和的条件下与原位形成的维斯迈试剂进行反应，并且广泛的底物范围可以兼容。28个样品成功地转化为相应的氯二氢萘，产率中等至较高，同时显著抑制了卤代烯醛副产物的形成。该方法简便、高效、底物相容性广，是合成卤化芳基烯烃和药物分子的一种很有前途的替代方法。2009爱思唯尔有限公司版权所有。

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来源期刊

Tetrahedron Letters 化学-有机化学

CiteScore

3.50

自引率

5.60%

发文量

521

审稿时长

28 days

期刊介绍： Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.