来自基的异环的原子经济合成
Barry M Trost1, Jean-Philip Lumb, Joseph M Azzarelli
1Department of Chemistry, Stanford University, Stanford, California 94305-5080, United States. bmtrost@stanford.edu
一种新的级联反应提供了一种简单而强大的方法来合成2,4-非替代的醇异环. 这种多功能方法耐受于空气和水分,在环境温度下有效运行.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
- 异环化学 异环化学
背景情况:
- 醇异环是药物化学和材料科学中的关键支架.
- 开发高效和多功能合成路径以取代pyrroles仍然是一个活跃的研究领域.
研究的目的:
- 报告一种新型的级联反应,用于合成2,4-非替代的醇异环.
- 为了证明开发的合成方法的操作简单性和稳定性.
主要方法:
- 采用了一种级联反应策略.
- 反应的特点是它对空气和水分的耐受性.
- 合成是在环境温度下进行的.
主要成果:
- 成功建立了一条可靠的途径,以获得2,4-非替代型醇异环.
- 反应条件允许对各种醇衍生物进行受控访问.
- 合成了异皮醇,2,3,4-三位替代的皮醇和3位替代的皮洛利丁-2-.
结论:
- 报告的级联反应提供了一种简单而有效的方法,用于访问多种类型的pyrrole结构.
- 操作简单和温和的条件使其成为合成化学家的宝贵工具.
- 这种方法扩大了合成工具包,用于构建复杂的异环化合物.
更多相关视频
09:58Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
09:54Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
Published on: September 12, 2018
相关概念视频
Structure and Physical Properties of Alkynes
In nature, compounds containing both carbon and hydrogen are known as "hydrocarbons". Aliphatic hydrocarbons are compounds whose molecules contain saturated single bonds (i.e., alkanes) or unsaturated double or triple bonds. Alkenes contain carbon–carbon double bonds and have a structural formula CnH2n. Unsaturated hydrocarbons containing carbon–carbon triple bonds are called "alkynes" and are structurally represented by the formula CnH2n-2.
The simplest alkyne is ethyne, or...
Electrophilic Addition to Alkynes: Halogenation
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Nomenclature of Alkynes
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.
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.
