一个没有醇的途径到基基乙烯乙烯
Dmitry I Bugaenko1, Alexey A Volkov1, Alexander V Karchava1
1Department of Chemistry, Moscow State University, Moscow 119991, Russia.
这项研究引入了一种新的,简单的无醇方法,用于合成使用二利盐和酸盐的基基乙烯. 这种方法提供了高的功能组耐受性,并使后期的C-H功能化.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
背景情况:
- 传统的基基乙烯基乙烯的合成通常依赖于默卡坦,这带来了实际的挑战和安全问题.
- 开发替代性,更容易获得的合成路线对于推进有机合成至关重要.
研究的目的:
- 建立一个操作简单和无醇的方法来合成基基乙烯.
- 为了证明diaryliodonium盐和xanthate盐在这种转化中的实用性.
- 探索开发的方法在后期功能化和deuteromethylthiolation中的应用.
主要方法:
- 迪亚利多盐与酸盐的反应,这些盐很容易从酒精和二硫化碳 (CS2) 中制备.
- 反应条件的优化,以实现高产量和功能组耐受性.
- 该协议的应用用于后期阶段的C-H功能化和CD3S组的引入.
主要成果:
- 成功开发了一种新的,高效的,不含醇的合成途径,以获得基基乙醇.
- 该方法表现出广泛的功能组耐受性,允许合成复杂分子.
- 成功实现了后期C-H功能化和引入二甲基 (CD3S) 组,突出了该协议的多功能性.
结论:
- 开发的协议提供了一个实用和多功能替代方案,用于合成基基乙烯.
- 这种方法克服了与传统的基于硫醇的合成方法相关的局限性.
- 该协议在后期功能化和二甲基甲基化解中的适用性扩大了其在药物化学和材料科学中的实用性.
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相关概念视频
Preparation and Reactions of Sulfides
Preparation and Reactions of Thiols
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.
Conversion of Alcohols to Alkyl Halides
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 Alcohols via Substitution Reactions
Alcohols can be synthesized from alkyl halides via nucleophilic substitution reactions. The highly polar carbon-halogen bond in the substrate makes halide a good leaving group. The hydroxide ion or water can act as a nucleophile to take the place of halide and form an alcohol. The substitution reactions occur via two different reaction pathways, SN1 or SN2, depending on the nature of carbon attached to the halide.
Primary alcohols are synthesized from primary alkyl halides, and the...
