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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

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The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism01:13

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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.
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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.
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Updated: Jun 3, 2026

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
07:06

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

Published on: February 16, 2020

Titanium-catalyzed esterification and transesterification reactions facilitated using microwave heating.

William G Devine1, Nicholas E Leadbeater, Linda A Jacob

  • 1Department of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, CT 06269-3060, USA.

Future Medicinal Chemistry
|March 24, 2011
PubMed
Summary
This summary is machine-generated.

A new titanium-catalyzed method enables rapid ester synthesis using microwave heating. This approach efficiently produces various esters, even with acid-sensitive compounds, offering a valuable laboratory alternative.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Green Chemistry

Background:

  • Esters exhibit biological activity and are used to enhance drug delivery.
  • Traditional acid-catalyzed esterification faces limitations with acid-sensitive substrates and side reactions.

Purpose of the Study:

  • To develop an alternative esterification and transesterification method.
  • To provide a milder and more efficient synthesis route for esters.

Main Methods:

  • Titanium-catalyzed esterification and transesterification.
  • Utilized microwave heating for accelerated reactions.

Main Results:

  • Reactions completed within 1 hour at 160 °C.
  • Successfully synthesized esters from aromatic, aliphatic, and heteroaromatic acids.
  • Accommodated acid-sensitive alcohols, such as furfuryl alcohol.

Conclusions:

  • A versatile methodology for ester preparation using titanium catalysis and microwave heating.
  • Efficiently produces a range of esters, including those from sensitive precursors.