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Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration02:40

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration

10.9K
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.
10.9K
Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

9.0K
Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
9.0K
Acidity of 1-Alkynes02:42

Acidity of 1-Alkynes

11.3K

The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
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Acid-Catalyzed Hydration of Alkenes02:45

Acid-Catalyzed Hydration of Alkenes

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Alkenes react with water in the presence of an acid to form an alcohol. In the absence of acid, hydration of alkenes does not occur at a significant rate, and the acid is not consumed in the reaction. Therefore, alkene hydration is an acid-catalyzed reaction.
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Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis01:13

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis

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Hydrolysis of esters under acidic conditions proceeds through a nucleophilic acyl substitution. In the presence of excess water, the reaction proceeds in a reversible manner, forming carboxylic acids and alcohols.
During hydrolysis, the ester is first activated towards nucleophilic attack through the protonation of the carboxyl oxygen atom by the acid catalyst. The protonation makes the ester carbonyl carbon more electrophilic. In the next step, water acts as a nucleophile and adds to the...
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Acid-Catalyzed Dehydration of Alcohols to Alkenes02:35

Acid-Catalyzed Dehydration of Alcohols to Alkenes

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In a dehydration reaction, a hydroxyl group in an alcohol is eliminated along with the hydrogen from an adjacent carbon. Here, the products are an alkene and a molecule of water. Dehydration of alcohols is generally achieved by heating in the presence of an acid catalyst. While the dehydration of primary alcohols requires high temperatures and acid concentrations, secondary and tertiary alcohols can lose a water molecule under relatively mild conditions.
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  2. アルキンの選択的パラジウム触媒カルボニレーション: 1,4-デカルボキシル酸ダイステルの原子経済的な合成
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  2. アルキンの選択的パラジウム触媒カルボニレーション: 1,4-デカルボキシル酸ダイステルの原子経済的な合成

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Synthesis Method for Cellulose Nanofiber Biotemplated Palladium Composite Aerogels
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Synthesis Method for Cellulose Nanofiber Biotemplated Palladium Composite Aerogels

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アルキンの選択的パラジウム触媒カルボニレーション: 1,4-デカルボキシル酸ダイステルの原子経済的な合成

Jiawang Liu1, Kaiwu Dong1, Robert Franke2,3

  • 1Leibniz-Institut für Katalyse e.V. an der Universität Rostock , Albert-Einstein-Str. 29a , Rostock , 18059 , Germany.

Journal of the American Chemical Society
|July 24, 2018

PubMed で要約を見る

まとめ
この要約は機械生成です。

新しいディフォスフィンのリガンドは,アルキンからダイステルの選択的合成を可能にします. リガンド選択は,1,4-二酸化炭素ダイステルまたはα,β-不飽和エステルの生成を制御する.

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

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

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Synthesis Method for Cellulose Nanofiber Biotemplated Palladium Composite Aerogels
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Synthesis Method for Cellulose Nanofiber Biotemplated Palladium Composite Aerogels

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

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 2014

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科学分野:

  • 有機金属化学
  • カタリシス
  • 有機合成

背景:

  • ディフォスフィン・リガンドは移行金属の触媒に不可欠です.
  • アルキンの機能化における選択性を制御することは依然として課題である.

研究 の 目的:

  • ピリジン置換剤を用いた新しいディフォスフィン結合体を設計し合成する.
  • パラジウム触媒によるアルキン炭化反応におけるその応用を探求する.

主な方法:

  • 新型ディフォスフィンの合成
  • パラジウム複合体の形成と特徴付け
  • アルキンの化学的および地域選択的ダイアルコキシカルボニレーション.
  • 反応メカニズムの運動研究

主要な成果:

  • 新しいピリジン置換型ディフォスフィンの合成に成功した.
  • パラジウム複合体は,アルキンの化学的および地域選択的ダイアルコキシカルボニレーションを触媒とした.
  • 1,4-二酸化炭素ダイステルの高い収量と選択性が得られた.
  • リガンド改変により,選択性をα,β-不飽和エステルに切り替える事が可能になった.

結論:

  • 新しく開発されたディフォスフィン・リガンドは,アルキンの機能化に精密な制御を提供します.
  • 開発された触媒システムは,多様なダイエスター製品にアクセスできます.
  • 反応運動の理解は,触媒的結果の最適化に役立ちます.