N-heterocyclic carbene-catalyzed nucleophilic aromatic substitution reaction of polyfluoroarenes

IF 1.8 3区 化学 Q3 CHEMISTRY, ORGANIC
Lishuai Lu , Dengyu Yin , Xiao-Xuan Li , Yandong Dou , Yanwu Zhu , Shilu Fan
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引用次数: 0

Abstract

Fluorinated asymmetric aryl ketones represent a pivotal class of organic synthesis intermediates, which have garnered widespread application in the realms of organic chemistry, materials science, and drug discovery. Herein, we report a pioneering nucleophilic aromatic substitution (SNAr) reaction involving aryl aldehydes and polyfluoroarenes, elegantly catalyzed by N-heterocyclic carbene (NHC). This innovative strategy yields bis(hetero)aryl ketone products in yields ranging from moderate to exceptional (40–83%), all achieved under gentle conditions, devoid of both transition metals and directing groups. The versatility of this method is underscored by its compatibility with a broad spectrum of substrates, particularly exhibiting remarkable resilience toward alkoxy functional groups. Notably, we have successfully transformed an array of biologically active molecules, crafting a series of their corresponding derivatives with precision.

N- 异环碳烯催化的多氟烯烃亲核芳香取代反应
氟化不对称芳基酮是一类重要的有机合成中间体,在有机化学、材料科学和药物发现领域得到了广泛的应用。在此,我们报告了一个开创性的亲核芳香取代(SNAr)反应,该反应涉及芳基醛和多氟烯烃,由 N-杂环碳烯(NHC)优雅地催化。这种创新策略可以产生从中等到极高产率(40-83%)的双(杂)芳基酮产品,所有这些都是在温和的条件下实现的,既没有过渡金属,也没有指导基团。这种方法的多功能性体现在它与多种底物的兼容性上,尤其是对烷氧基官能团具有显著的适应性。值得注意的是,我们已经成功地转化了一系列生物活性分子,并精确地制作出一系列相应的衍生物。
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来源期刊
Synthetic Communications
Synthetic Communications 化学-有机化学
CiteScore
4.40
自引率
4.80%
发文量
156
审稿时长
4.3 months
期刊介绍: Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.
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