帕拉催化双脱碳 [3 + 2] 取消纳夫塔酸无水化物与内部基因的取消
Chaipot Kanganavaree1, Kritchasorn Kantarod1, Thanapat Worakul1
1Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Rd, Bangkok 10400, Thailand.
一种新的催化反应有效地从纳夫他尔无水化物和中合成1,2-非替代的乙甲烯. 这种方法提供了优异的功能组耐受性,并扩展到相关的伊米德基质.
科学领域:
- 有机合成 有机合成
- 催化剂是一种催化剂.
- 材料科学 材料科学 材料科学
背景情况:
- 纳酸无水化物是有机合成中的多功能前体.
- 开发高效的合成途径,以复杂的多环芳的发展对于材料科学应用至关重要.
研究的目的:
- 开发一种新的催化 [3 + 2] 无效反应.
- 合成具有高效率和功能组兼容性的1,2-非替代性乙乙烯.
- 探索将这种方法扩展到纳夫他林和佩里莱尼卡尔博克西米德衍生物.
主要方法:
- 帕拉催化 [3 + 2] 废除纳夫他尔无水化物与内部基.
- 使用X射线晶体学,紫外线和光光谱学对产品的表征.
- 使用密度函数理论 (DFT) 计算进行理论研究.
主要成果:
- 成功合成了一系列1,2-非替代的乙甲烯.
- 在取消反应中表现出优异的功能组耐受性.
- 将合成协议扩展到含有纳夫他林和 perylenedicarboximide 的基板.
结论:
- 已经建立了一种新且高效的催化取消协议,用于访问替代的乙甲基.
- 反应通过拟议的双脱碳化机制进行.
- 开发的方法为功能多环芳香化合物提供了有价值的合成策略.
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相关概念视频
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.
Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
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.
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.
Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
