通过Rh(III) 催化的化和化C-H与环醇的化通过C-H/C-C键激活
Om Prakash Dash1, Divya Garg1, Chandra M R Volla1
1Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai-400076, India. chandra.volla@chem.iitb.ac.in.
概括
这项研究引入了一种新的Rh(III) 催化方法,用于使用环醇进行C-H化. 这有助于有效合成有价值的β功能化和相关化合物.
科学领域:
- 有机化学 有机化学
- 催化剂是一种催化剂.
- 合成方法论 合成方法论
背景情况:
- C-H激活是现代有机合成的一个关键策略.
- 环醇为C-C键形成提供了独特的反应性.
- 开发高效的催化系统对于子合成仍然很重要.
研究的目的:
- 开发一种用于C-H化的新型Rh (III) 催化协议.
- 为了利用环醇作为C-C键激活的化剂.
- 合成β功能化子,包括1,4-二基和β-基.
主要方法:
- ((III) 催化反应的环醇与化物或anilines.
- 循环醇的C-C键激活.
- 探索反应范围和功能组容忍度.
主要成果:
- 成功合成了各种不对称的1,4-二基.
- 从素衍生物中有效制备β-基.
- 通过自然产品的修饰和格拉姆尺度合成来证明其实用性.
结论:
- 开发的协议提供了一条通往β功能化子的多功能途径.
- 该方法展示了广泛的基板范围和功能化后的潜力.
- 这项工作扩大了环醇在催化C-H功能化中的实用性.
相关概念视频
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones
3.7K
By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
3.7K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
2.1K
Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
2.1K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
7.7K
Introduction
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.
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.
7.7K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
17.9K
Introduction
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.
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.
17.9K
Electrophilic Addition to Alkynes: Hydrohalogenation
9.8K
Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
9.8K
Base-Promoted α-Halogenation of Aldehydes and Ketones
3.4K
α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base. The reaction begins with the abstraction of α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...
3.4K


