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相关概念视频

Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

20.7K
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.
20.7K
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

11.1K
In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
11.1K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

7.3K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
7.3K
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

7.4K
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
7.4K
Alcohols from Carbonyl Compounds: Reduction02:23

Alcohols from Carbonyl Compounds: Reduction

12.1K
Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...
12.1K

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Updated: Jan 18, 2026

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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稳定的BF2 Boracycles作为选择性整形C-H功能化的多功能试剂.

Ganesh H Shinde1, Jonatan Babiker1, Michelle Mebrahtu1

  • 1Department of Chemistry and Molecular Biology, University of Gothenburg, Gothenburg, Sweden, SE-41296.

Angewandte Chemie (International ed. in English)
|January 17, 2026
PubMed
概括

研究人员开发了一种可扩展的,无金属的方法,用于稳定的BF2环,在有机合成中很有价值. 这些化合物使复杂分子结构的多种功能化和交叉合反应成为可能.

关键词:
BBr3 在线阅读(Boron) 是一种的物质.交叉合方式的交叉合方式.后期阶段的功能化功能化.放射性染是一种放射性染.

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科学领域:

  • 有机化学 有机化学
  • 合成有机化学 合成有机化学

背景情况:

  • 试剂对于现代有机合成至关重要,特别是在C-H功能化和交叉合中.
  • 开发稳定和反应性物种是有效合成策略的关键.

研究的目的:

  • 建立一个无金属,可扩展的协议,用于合成稳定的BF2玻拉环.
  • 为了证明这些BF2环作为有机合成中的多功能中间体的实用性.

主要方法:

  • 开发了一种强大的,无染色体的,BF2波拉循环的多图合成.
  • 在ipso-substitution反应中研究了BF2环的反应性.
  • 评估了他们在木-米亚乌拉交叉合反应中的表现.

主要成果:

  • 实现了一条实用而有效的途径,稳定了BF2玻拉单车.
  • 已证明成功的ipso-substitution产生基,基和酸衍生物.
  • 在 Suzuki-Miyaura 合中表现出极好的反应性,用于 C sp2 - C sp2 和 C sp2 - C sp3 键形成.

结论:

  • BF2环是稳定的,用于晚期多样化的反应性中间体.
  • 这种方法为药物合成和复杂分子构造提供了对有机化合物的简化方法.
  • 代表了有机化学的重大进步,具有广泛的适用性.