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Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

3.2K
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.
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Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

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Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
2.6K
Preparation of Amines: Alkylation of Ammonia and Amines01:30

Preparation of Amines: Alkylation of Ammonia and Amines

3.9K
Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
3.9K
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

7.5K
The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
7.5K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

2.7K
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
2.7K
Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

2.3K
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,...
2.3K

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Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
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調節可能な,銀触媒による化学選択性アミネーション.

Jared W Rigoli1, Cale D Weatherly, Juliet M Alderson

  • 1Department of Chemistry, University of Wisconsin , Madison, Wisconsin 53706, United States.

Journal of the American Chemical Society
|November 6, 2013
PubMed
まとめ

研究者らは,選択的有機アミナ化反応のための新しい銀ベースの触媒を開発した. この触媒は,C-H挿入またはアジリジネーションを正確に制御し,窒素を含む化合物を合成するための新しいツールを提供します.

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
  • 薬用化学 薬用化学について

背景:

  • アミンのような窒素を含む有機化合物は,多くの生物学的活性および医薬品分子にとって不可欠な構成要素です.
  • 有機分子に窒素を導入するには,通常C-H結合の挿入または炭素-炭素二重結合の添加を通じて,反応性ナイトレンまたはナイトレノイド種がしばしば含まれます.
  • よく定義された触媒を用いた予測可能で化学選択的なアミネーション反応を達成することは大きな課題であり,多くの場合,反応剤制御に大きく依存しています.

研究 の 目的:

  • 化学選択性アミネーション反応のための触媒システムを開発する.
  • 単一の触媒システムを使用して反応経路 (C-H挿入対アジリディネーション) の制御を実証する.
  • 反応結果の決定における触媒調整幾何学の役割を調査する.

主な方法:

  • 単一の金属 (銀) と単一のリガンド (フェナントロリン) を利用して,活性触媒を作製した.
  • 反応選択性に影響を与えるために触媒の調整幾何学の操作を調査した.
  • 化学選択性と効率性を評価するために,様々な有機基板にアミネーション反応を行った.

主要な成果:

  • シルバーフェナントロリン触媒システムを用いて,アミネーション反応で顕著な化学選択性を達成した.

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  • シルバー触媒の調整幾何学を変更することによって,選択的にC-H挿入またはアジリディネーションを促進する能力を実証しました.
  • 制御されたアミネーション経路を通じて窒素を含む有機化合物を成功して合成した.

    • 結論:

    • 単一のシルバーフェナントロリン触媒システムは,異なるアミネーション結果 (C-H挿入またはアジリディネーション) を達成するためにチューニングすることができます.
    • 触媒の調整幾何学は,窒素移転反応における化学選択性を制御する上で重要な要因である.
    • この研究は,有価な窒素を含む分子の制御された合成のための新しい戦略を提供します.