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関連する概念動画

Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...
Amines to Alkenes: Hofmann Elimination01:16

Amines to Alkenes: Hofmann Elimination

Alkenes can be obtained from amines via an E2 elimination. The amine is first converted into a good leaving group, such as a quaternary ammonium salt. This is accomplished by treating the amine with an excess of alkyl halide, which results in a halide salt. Next, the halide salt is transformed into a hydroxide salt that functions as a base to enable elimination.
Under thermal conditions, the hydroxide can abstract a proton from the β carbon; this generates an alkene with the simultaneous...
Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

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 to Amines: LiAlH4 Reduction01:20

Amides to Amines: LiAlH4 Reduction

Amide reduction with strong reducing agents like lithium aluminum hydride proceeds through a nucleophilic acyl substitution to form amines. Primary, secondary, and tertiary amides yield primary, secondary, and tertiary amines, respectively.
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.
Amines to Alkenes: Cope Elimination01:14

Amines to Alkenes: Cope Elimination

Cope elimination reaction involves the conversion of tertiary amines to alkene using hydrogen peroxide under thermal conditions, as depicted in figure 1.
Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

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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関連する実験動画

Updated: Jun 10, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
19:58

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

アリルパラジウム親アミド複合体からの緩やかな還元性除去.

Jessica L Klinkenberg1, John F Hartwig

  • 1Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, Illinois 61801, USA.

Journal of the American Chemical Society
|August 11, 2010
PubMed
まとめ

この研究は,特定のボリュームのあるリガンドを持つパラジウム複合体が,原発アリラミンの還元性除去を促進し,有機金属化学と触媒の以前の傾向に異議を唱えていることを示しています.

科学分野:

  • 有機金属化学 有機金属化学
  • カタリシス カタリシス カタリシス
  • オーガニック・シンセシス オーガニック・シンセシス

背景:

  • 還元性除去は多くの触媒サイクルにおける重要なステップですが,その効率はリガンドと基板の特性によって影響されます.
  • パラジウム複合体は,C-N結合形成を含むクロスカップリング反応で広く使用される触媒である.

研究 の 目的:

  • アリルパラジウム (II) の親アミド複合体から一次アリラミンの還元性除去を調査する.
  • これらの複合体の形成,安定性,および反応性に対するビスホスフィンリガンドの影響を理解する.

主な方法:

  • ビスホスフィン結合アリルパラジウム ((II) 親アミド複合体の合成と特徴付け.
  • 還元性除去反応の運動学的研究.
  • 反応機構とステリック効果を明らかにするための計算研究 (DFTなど)

主要な成果:

  • アルキルビスホスフィンで結合されたアリルパラジウム親アミド複合体は,CyPF-t-Buを形成し,芳香ビスホスフィン (DPPF,BINAP) によるものとは異なり,還元性除去を受けます.
  • CyPF-t-Bu結合複合体は,親アミドリガンドの塩基性にもかかわらず,アリラミドまたはアルキラミド類似体と比較して,より遅い還元性除去率を示します.
  • 親アミド複合体は,アリラミド複合体よりも,より速い形成とより高い熱力学的安定性を示します.

さらに関連する動画

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
11:44

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents
07:20

Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents

Published on: May 28, 2014

関連する実験動画

Last Updated: Jun 10, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
19:58

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
11:44

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents
07:20

Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents

Published on: May 28, 2014

  • 計算学的研究によって支持されるステリック効果は,これらの複合体の安定性と反応性において支配的な役割を果たします.

    • 結論:

    • 大量のアルキルビスホスフィンのリガンドであるCyPF-t-Buは,アリルパラジウムアミド複合体を安定させ,アリルハリドがアンモニアと結合した状態の静止状態にします.
    • この発見は,Pd(0) またはアリルパラジウム(II) 種がしばしば静止状態である典型的なパラジウム触媒化アミネーション反応と対照的です.
    • リガンドのステリックの影響は,パラジウム触媒化アミネーション反応における反応性の制御に極めて重要です.