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Related Concept Videos

Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

2.8K
Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
6.2K
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism01:13

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism

8.1K
Carboxylic acids react with alcohols to yield esters via an acid-catalyzed condensation reaction called Fischer esterification. This is a nucleophilic acyl substitution reaction that proceeds via a tetrahedral intermediate, where a water molecule is eliminated as the leaving group.
8.1K
Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis01:13

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis

3.1K
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...
3.1K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.4K
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...
3.4K
Carboxylic Acids to Acid Chlorides01:18

Carboxylic Acids to Acid Chlorides

7.1K
Carboxylic acids react with SOCl2 or PCl5 to form acid chlorides. Amongst the carboxylic acid derivatives, acid chlorides are the most reactive and synthetically important derivatives. They are useful reagents for Friedel–Crafts acylation of some aromatic compounds.
7.1K

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Asymmetric Fluorocyclization of Difluoroalkenes with Concomitant Formation of a Trifluoromethyl Group.

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Asymmetric Fluorofunctionalizations with Carboxylate-Based Phase-Transfer Catalysts.

Hiromichi Egami1, Yoshitaka Hamashima1

  • 1School of Pharmaceutical Sciences, University of Shizuoka 52-1 Yada, Suruga-ku, Shizuoka, 422-8526, Japan.

Chemical Record (New York, N.Y.)
|February 3, 2023
PubMed
Summary
This summary is machine-generated.

Researchers developed chiral phase-transfer catalysts for asymmetric fluorocyclizations. These catalysts enable the synthesis of valuable chiral fluorinated compounds from alkenes using Selectfluor, with applications in pharmaceuticals and agrochemicals.

Keywords:
asymmetric reactiondearomatizationdifunctionalizationfluorinationphase-transfer catalyst

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Asymmetric Synthesis

Background:

  • Fluorine incorporation enhances pharmaceutical and agrochemical properties.
  • Chiral fluorinated compounds are crucial due to enantiomer-specific biological activities.
  • Developing efficient methods for asymmetric fluorination is a key research area.

Purpose of the Study:

  • To develop novel chiral carboxylate-based phase-transfer catalysts.
  • To apply these catalysts for asymmetric fluorocyclizations of alkenes.
  • To explore dearomative fluorinations of various aromatic systems.

Main Methods:

  • Development of chiral carboxylate-based phase-transfer catalysts.
  • Asymmetric fluorocyclization of alkenes using Selectfluor.
  • Dearomative fluorination of indole derivatives, 2-naphthols, and resorcinols.

Main Results:

  • Successfully synthesized chiral fluorinated compounds via asymmetric fluorocyclization.
  • Demonstrated catalyst efficacy with various internal nucleophiles (carboxylic acid, amide, oxime).
  • Achieved dearomative fluorination of diverse aromatic substrates.

Conclusions:

  • Chiral phase-transfer catalysis offers an effective route to enantiomerically enriched fluorinated molecules.
  • The developed catalysts are versatile for both cyclization and dearomative fluorination reactions.
  • This work provides valuable tools for accessing complex fluorinated organic compounds.