コバルト単原子触媒による機能性エタン-1,2-ダイアミンの一般合成のためのニトロアレンとHCHOの還元結合
Jia-Lu Sun, Huanfeng Jiang, Pierre H Dixneuf1
1Université de Rennes, CNRS, ISCR UMR 6226, 35000 Rennes, France.
Journal of the American Chemical Society
|July 7, 2023
まとめ
新しい方法は,コバルト単原子触媒 (CoSA-N/NC) と容易に入手可能なニトロアレンとホルモアルデヒドを使用してN,N-ダイアリエタン-1,2-アミンを合成します. この効率的なプロセスは,広範囲の基板互換性と触媒の再利用性を提供します.
科学分野:
- カタリシス
- 有機合成
- 材料科学
背景:
- N,N'-ダイアリレタン-1,2-ダイアミンの選択的合成は難しい.
- 既存の方法はしばしば効率的でないか,基板の範囲がない.
研究 の 目的:
- N,N'-ダイアリレタン-1,2-ダイアミンを合成するための一般的で効率的な方法を開発する.
- 新しい二機能コバルト単原子触媒 (CoSA-N/NC) を利用する.
主な方法:
- CoSA-N/NC触媒を用いたニトロアレンとフォーマルデヒドの直接的還元結合
- N-アンコールコバルト単一原子 (CoN4) とN-ドープされた炭素サポートを含むメカニズム研究.
- 逆電子需要 1,3-二極サイクロアディションと水酸化ステップ.
主要な成果:
- N,N'-ダイアリレタン-1,2-ダイアミンの合成が成功し,基板と機能の互換性が良好です.
- 触媒の再利用性と高いステップ/原子効率が実証されている.
- "in situ"で生成された構成要素を含む触媒メカニズムを明らかにした.
結論:
- CoSA-N/NC触媒は,価値あるダイアミンを合成するための一般的で効率的で再利用可能な方法を提供します.
- 触媒制御によるニトロアレンを特定の構成要素に還元することで,新しい化学的変換の道が開けます.
さらに関連する動画
関連する概念動画
01:38Preparation of Amines: Reductive Amination of Aldehydes and Ketones
2.9K
Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
2.9K
01:29Preparation of Amines: Reduction of Oximes and Nitro Compounds
3.8K
Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
3.8K
00:55Nitriles to Amines: LiAlH4 Reduction
3.6K
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...
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...
3.6K
01:13Preparation of Amines: Reduction of Amides and Nitriles
2.5K
Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an amino group with an extra carbon in the skeleton. Nitriles are formed from the reaction between alkyl halides and sodium cyanide through the SN2 mechanism. Primary alkyl halides are the preferred substrates to prepare nitriles.
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...
2.5K
02:24Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
7.8K
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.
7.8K
01:26Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
3.4K
α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.
3.4K