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Related Concept Videos

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis01:13

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis

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

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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...
Esters to Alcohols: Hydride Reductions01:17

Esters to Alcohols: Hydride Reductions

Esters are reduced to primary alcohols when treated with a strong reducing agent like lithium aluminum hydride. The reaction requires two equivalents of the reducing agent and proceeds via an aldehyde intermediate.
Lithium aluminum hydride is a source of hydride ions and functions as a nucleophile. The mechanism proceeds in three steps. Firstly, the nucleophilic hydride ion attacks the carbonyl carbon of the ester to form a tetrahedral intermediate. Subsequently, the carbonyl group re-forms,...
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the surface of...
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction 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.
Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.

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Updated: May 15, 2026

Light-driven Enzymatic Decarboxylation
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Light-driven Enzymatic Decarboxylation

Published on: May 22, 2016

Pd-catalyzed aldehyde to ester conversion: a hydrogen transfer approach.

Brittany A Tschaen1, Jason R Schmink, Gary A Molander

  • 1Roy and Diana A. Vagelos Laboratories and Penn/Merck Laboratory for High Throughput Experimentation, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.

Organic Letters
|January 17, 2013
PubMed
Summary

This study presents a new method for converting aldehydes to esters using palladium acetate and XPhos. The process uses a sustainable hydrogen transfer from acetone, avoiding harsh oxidants.

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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

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Last Updated: May 15, 2026

Light-driven Enzymatic Decarboxylation
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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

Published on: February 16, 2020

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Sustainable Chemistry

Background:

  • Aldehyde transformations are crucial in organic synthesis.
  • Existing methods often require harsh oxidants or complex procedures.
  • Development of sustainable catalytic methods is a key research area.

Purpose of the Study:

  • To develop an efficient and sustainable method for converting aliphatic and aromatic aldehydes into their corresponding esters.
  • To utilize a hydrogen transfer protocol for this transformation.
  • To avoid the use of stoichiometric oxidants.

Main Methods:

  • Utilized palladium(II) acetate (Pd(OAc)2) as the catalyst.
  • Employed XPhos as a ligand.
  • Implemented a hydrogen transfer reaction using acetone as the hydrogen source.
  • Reduced aldehydes to esters.

Main Results:

  • Successfully converted a range of aliphatic and aromatic aldehydes to their respective esters.
  • Achieved high yields and selectivity in the esterification reactions.
  • Demonstrated the concomitant reduction of acetone to isopropanol, acting as the hydrogen source.
  • Showcased an oxidant-free synthetic approach.

Conclusions:

  • The developed Pd-catalyzed method offers an efficient and sustainable route for aldehyde esterification.
  • The use of acetone as a hydrogen donor provides an inexpensive and environmentally friendly alternative to traditional oxidants.
  • This approach represents a significant advancement in green chemistry for ester synthesis.