関連する実験動画
Updated: May 20, 2026
08:43
Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
銅で触媒化された非活性アルケンのオキシトリフルオロメチル化
1Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
Journal of the American Chemical Society
|July 19, 2012
まとめ
新しい銅触媒法により,アルケーンにトリフローロメチル基を効率的に添加する. この多用途なテクニックは,シンプルな出発材料から有用なCF(3) 含有化合物を作成します.
科学分野:
- 有機化学 オーガニック・ケミストリー
- カタリシス カタリシス カタリシス
- フロアンの化学的性質
背景:
- トリフルオロメチル (CF(3) を含む化合物は,医薬品と材料科学において重要である.
- CF(3) グループを導入するための効率的な方法は,非常に求められています.
- 既存の方法は,しばしば厳しい条件や特殊な反応剤を必要とします.
研究 の 目的:
- 活性化されていないアルケンのオキシトリフルオロメチル化のための温和で,多用途で,便利な方法を開発する.
- 銅で触媒化された酸化機能低下戦略を活用する.
- 合成的に有用なCF(3) を含む構成要素へのアクセスを提供するために.
主な方法:
- 銅で触媒化された酸化機能低下.
- 活性化されていないアルケンのトリフローロメチル源と酸化物質との反応.
- 軽度の反応条件.
主要な成果:
- 活性化されていないアルケンの範囲の効率的なオキシトリフルオロメチル化.
- CF ((3) を含む様々な構成要素の合成が成功しました.
- 汎用的で便利な方法論の実証.
結論:
- アルケンのオキシトリフルオロメチル化のための新しい効率的な方法が確立されています.
- 開発された戦略は,CF(3) を含む化合物への貴重な経路を提供します.
- この方法論は,有機フッ素分子を合成するためのツールキットを拡張します.
関連する概念動画
02:36Oxymercuration-Reduction of Alkenes
Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.
03:08Hydroboration-Oxidation of Alkenes
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.
02:44Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
01:22Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
02:47Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
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.
01:46Oxidative Cleavage of Alkenes: Ozonolysis
In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.