级联利化/迪尔斯-阿尔德循环添加的alkynylindoles与缺电子的和
Guang-Chao Feng1, Jun-Chi Li1, Xiang Huang1
1School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan 430074, People's Republic of China. jmyang@scuec.edu.cn.
这项研究引入了一种新的黄金催化反应,它结合了水利化和迪尔斯-阿尔德循环添加. 有效合成有价值的 azepino-fused 碳化合物和碳化合物是通过高原子经济实现的.
科学领域:
- 有机化学 有机化学
- 催化剂是一种催化剂.
- 异环化学 异环化学
背景情况:
- 基尼林多尔是有机合成中的多功能构建块.
- 黄金催化已经成为形成C-C键的强大工具.
- 迪尔斯-阿尔德反应对于构建循环系统至关重要.
研究的目的:
- 开发一种新型的级联反应,用于合成复杂的异环化合物.
- 为了探索黄金的实用性 (I) 催化在一个并联化-迪尔斯-阿尔德序列.
- 为了有效地获取与阿泽皮诺融合的碳化合物和碳化合物.
主要方法:
- 级黄金 ((I) 催化化的基尼林多尔.
- 随后的迪尔斯-阿尔德循环添加与缺电子的基和基.
- 反应条件的优化,包括催化剂负荷和温度.
主要成果:
- 成功合成了多种与阿泽皮诺融合的碳化合物和碳化合物.
- 在目标化合物中获得中等到优异的产量.
- 证明了高的区域选择性和广泛的功能群耐受性.
结论:
- 开发的级联反应提供了一个有效的途径,以重要的异环基架.
- 该方法具有较低的催化剂负载和100%的原子经济.
- 这种方法为进一步的化学勘探提供了获取有价值化合物的途径.
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相关概念视频
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
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.
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Cycloaddition Reactions: Overview
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.
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.
