トリアゾール-Au(I) コンプレックス: 熱安定性と反応性の向上により,分子間アルキンヒドロアミネーションの新種の触媒です
Haifeng Duan1, Sujata Sengupta, Jeffrey L Petersen
1C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.
Journal of the American Chemical Society
|August 7, 2009
まとめ
トライアゾールリガンドを含む新金 ((I) 触媒は,熱安定性を高め,触媒を少なく使って非反応性基質の複雑な分子間水素酸化を可能にします.
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
- 合成化学 合成化学とは
背景:
- 金 ((I) 触媒は,様々な有機変異に有効である.
- 現存する黄金触媒は,限られた熱安定性に苦しむ可能性があります.
- ハイドロアミネーション反応は,アミンの合成に不可欠です.
研究 の 目的:
- 新しい1,2,3-トリアゾール結合カチオン金 (((I)) 触媒の合成と特徴づけ.
- これらの新しい金複合物の熱安定性と触媒性能を評価するために.
- 反応性が低い基質で複雑な分子間ヒドロアミネーションを達成するために.
主な方法:
- 金 (((I) 複合物の合成とX線結晶学.
- 温度変数核磁共振 (NMR) スペクトロスコーピー. 温度変数核磁共振 (NMR) スペクトロスコーピー.
- 分子間ヒドロアミネーション反応の触媒試験.
主要な成果:
- 新しい1,2,3-トリアゾール結合のカチオン金 (((I) 触媒が成功して合成され,特徴づけられました.
- これらの触媒は,既存の金触媒と比較して優れた熱安定性を発揮します.
- 内部アルキンと保護されていないアリファティックアミンの複雑な分子間ヒドロアミナーションは,低触媒負荷で優れた収量で達成されました.
結論:
- 開発された金 ((I) 触媒は,熱安定性と触媒活性が向上しています.
- これらの触媒は,価値あるアミン化合物を合成するための効率的な方法を提供します.
- この発見は,複雑な有機合成において,黄金の触媒を活用するための新たな道を開く.
関連する概念動画
02:24Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
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.
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.
01:22Preparation of 1° Amines: Azide Synthesis
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...
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...
02:38Electrophilic Addition to Alkynes: Halogenation
Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
02:40Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration
Introduction
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
02:27Preparation of Alkynes: Alkylation Reaction
Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.