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Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

9.9K
Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
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Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

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By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
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Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

Base-Promoted α-Halogenation of Aldehydes and Ketones

3.4K
α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...
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Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

10.1K
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.
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Oxymercuration-Reduction of Alkenes02:36

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Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.
7.5K
Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate02:21

Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate

11.3K
Alkenes can be dihydroxylated using potassium permanganate.  The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.
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Three-Component Gold(I)-Catalyzed Alkoxyvinylation.

L Anders Hammarback1, Tania Medina-Gil1,2, Anna Sadurní1

  • 1Institute of Chemical Research of Catalonia (ICIQ), Barcelona Institute of Science and Technology (BIST), 43007 Tarragona, Spain.

Organic Letters
|July 18, 2024
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Summary
This summary is machine-generated.

This study introduces a novel gold(I)-catalyzed reaction using acetylene, alkenes, and alcohols. It efficiently synthesizes valuable β-vinyl hemiaminal scaffolds, expanding synthetic possibilities.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Acetylene is an underutilized but valuable feedstock in chemical synthesis.
  • Developing efficient catalytic methods for complex molecule construction is crucial.

Purpose of the Study:

  • To develop the first gold(I)-catalyzed intermolecular three-component reaction involving acetylene.
  • To synthesize β-vinyl hemiaminal scaffolds from N-vinyl amides, alkenes, and alcohols.

Main Methods:

  • Utilized a gold(I) catalyst for the intermolecular three-component reaction.
  • Employed acetylene, alkenes, and alcohols as reaction partners.
  • Investigated the synthesis of N-vinyl amides.

Main Results:

  • Successfully synthesized β-vinyl hemiaminal scaffolds.
  • Achieved the formation of unusual biscyclopropyl and 3-vinyl N-heterocyclic scaffolds.
  • Demonstrated versatility by incorporating a second N-vinyl unit or tethered alkene.

Conclusions:

  • The developed gold(I)-catalyzed reaction provides a novel route to valuable chemical scaffolds.
  • The methodology expands the synthetic utility of acetylene in organic chemistry.
  • The reaction offers access to complex heterocyclic structures previously difficult to obtain.