在催化过程中将基酸添加到酸中
Michinori Suginome1, Masamichi Shirakura, Akihiko Yamamoto
1Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University Katsura, Nishikyo-ku, Kyoto 615-8510, Japan. suginome@sbchem.kyoto-u.ac.jp
在催化过程中,用烯酸和烯酸对烯酸进行基化,从而产生cis-1-borylbut-1-en-3-yne衍生物. 这些中间体很容易经历苏子基-米亚乌拉合,产生高度结合的.
科学领域:
- 有机化学 有机化学
- 有机金属化学 有机金属化学
- 催化剂是一种催化剂.
背景情况:
- 基博化是有机合成中的一个关键转化.
- 催化为C-B键形成提供了独特的反应性.
- 结合酶是材料科学和药物化学中有价值的构建模块.
研究的目的:
- 为了开发一种新的催化基化反应.
- 为了合成来自基的cis-1-borylbut-1-en-3-yne衍生物.
- 在随后的合反应中证明这些玻利酸的实用性.
主要方法:
- 基基基基基基基基与终端基基的反应.
- 催化剂系统用于促进基化.
- 木-米亚乌拉交叉合玻利化因与sp2化物.
主要成果:
- 实现了1-aryl-1-alkynes的区域选择性基化.
- 在高产量中形成cis-1-borylbut-1-en-3-yne衍生物.
- 通过苏苏基-米亚乌拉合,合成高度合的恩因.
结论:
- 催化基化提供了有效的获取有价值的化中间体.
- 开发的方法为复杂的,高度结合的enyne结构提供了一条多功能途径.
- 这种方法扩大了基和催化剂的合成效用.
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相关概念视频
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.
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.
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.
Hydroboration-Oxidation of Alkenes
Electrophilic Addition to Alkynes: Hydrohalogenation
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.
