从基托,迪因和阿林,到功能化的皮拉,纳夫他林和人类
Angelika Mieszczanin1, Patrycja Filipek2, Anna Chrobok1
1Department of Chemical Organic Technology and Petrochemistry, Faculty of Chemistry, Silesian University of Technology, Krzywoustego 4, Gliwice, 44-100, Poland.
研究人员开发了一种简单的区域选择性合成,用于新型的aryl-arylethynyl-pyranones,naphthalenes和anthracenes. 这种创新方法可以获得独特的化合物,由于内置的三重键,具有可调节的特性.
科学领域:
- 有机合成 有机合成
- 材料科学 是一种材料科学.
- 催化剂是一种催化剂.
背景情况:
- 阿里尔-亚利利乙烯基衍生物是有机化学中有价值的构建模块.
- 这些化合物的现有合成途径通常是复杂的,缺乏效率.
- 需要新的,简单的方法来获得替代的pyranones,naphthalenes和anthracenes.
研究的目的:
- 开发新合成可能性的阿里尔-arylethynyl-naphthalene和anthracene衍生品.
- 为了建立一种创新的和高效的合成方法,以对aryl-arylethynyl-pyran-2-ones.
- 调查开发的合成程序的区域选择性和范围.
主要方法:
- 使用了诸如β-ketoesters,1,4-di(aryl,heteroaryl)buta-1,3-diynes和arynes等简单的起始材料.
- 采用由 (Re) 催化剂介导的一或两步程序.
- 使用DFT计算,热,光学和电化学分析来描述新合成的化合物.
主要成果:
- 通过简单而高效的程序,成功合成了新型的aryl-arylethynyl-pyran-2-ones,naphthalenes 和 anthracenes.
- 开发了一种完全区域选择的方法,只能获得5-aryl-4-(arylethynyl) -3,6-dimethylpyran-2-ones.
- 证明了固体效应在重新催化反应中影响区域选择性.
- 获得的化合物具有独特的特性,受三重键的存在影响.
结论:
- 开发的合成途径提供了前所未有的获取有价值的-乙烯基替代化合物的途径.
- 该程序比之前报告的方法要简单和方便得多.
- 合成的化合物具有独特的热,光学和电化学特性,使其具有进一步应用的吸引力.
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相关概念视频
Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Preparation of Alkynes: Dehydrohalogenation
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview
Nomenclature of Alkynes
