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関連する概念動画

Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

9.4K
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.
9.4K
Alcohols from Carbonyl Compounds: Reduction02:23

Alcohols from Carbonyl Compounds: Reduction

11.2K
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...
11.2K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

8.6K
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...
8.6K
Acid Halides to Ketones: Gilman Reagent01:14

Acid Halides to Ketones: Gilman Reagent

3.4K
Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen...
3.4K
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

4.0K
Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
4.0K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

19.3K
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.
19.3K

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関連する実験動画

Updated: Oct 23, 2025

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
09:45

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents

Published on: November 12, 2016

31.5K

ボライミノリチウム:イミノボラン移転反応剤

Rui Guo1, Tong Li1, Rui Wei2

  • 1School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China.

Journal of the American Chemical Society
|August 24, 2021
PubMed
まとめ

研究者は安定したボライミノリチウムを合成し,リチウムアセチリドの新型BN類である. この化合物は新しいイミノボラン転送反応を可能にし,化学と材料科学のためのユニークなBNを含む分子を作成します.

さらに関連する動画

1,3,5-Triphenylbenzene and Corannulene as Electron Receptors for Lithium Solvated Electron Solutions
06:56

1,3,5-Triphenylbenzene and Corannulene as Electron Receptors for Lithium Solvated Electron Solutions

Published on: October 10, 2016

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Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
10:14

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography

Published on: May 16, 2014

12.7K

関連する実験動画

Last Updated: Oct 23, 2025

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
09:45

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents

Published on: November 12, 2016

31.5K
1,3,5-Triphenylbenzene and Corannulene as Electron Receptors for Lithium Solvated Electron Solutions
06:56

1,3,5-Triphenylbenzene and Corannulene as Electron Receptors for Lithium Solvated Electron Solutions

Published on: October 10, 2016

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Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
10:14

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography

Published on: May 16, 2014

12.7K

科学分野:

  • 合成無機化学
  • 有機金属化学
  • メイングループ化学

背景:

  • ボロン-窒素 (BN) イソステリスムは,ユニークな分子特性を提供しています.
  • アルキニルリチウム化合物は,よく確立された合成反応剤です.
  • 安定したBNアナログの合成は活発な研究分野である.

研究 の 目的:

  • 新種のボライミノリチウムの合成と特徴を報告する.
  • この新しいBN化合物の反応性と合成有用性を調査する.
  • 化学と材料科学の基礎となる可能性を探求する.

主な方法:

  • デヒドロハロゲネーションとデプロトネーションの反応が合成に使用された.
  • 特徴付けには,光学および結晶学的技術が使われました.
  • 反応性の研究は,イミノボラン移転反応に焦点を当てた.

主要な成果:

  • 室温に安定する結晶型ボライミノリチウム種 (2) が成功して合成された.
  • この種はアルキニルリチウム分子の最初のBNアナログです.
  • N機能化されたイミノボランとメイングループヘテロサイクルを生成する効率的なイミノボラン転送反応を示した.

結論:

  • 安定したボライミノリチウム反応剤は,BN化学の重要な進歩を表しています.
  • これらの反応剤は,新しいBNを含む化合物にアクセスするための多用途のプラットフォームを提供します.
  • 合成化学と材料科学に潜在的応用がある.