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

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

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.
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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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...
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Oxymercuration-Reduction of Alkenes02:36

Oxymercuration-Reduction of Alkenes

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.
Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism01:14

Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism

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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
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Published on: March 20, 2014

An efficient dehydroxymethylation reaction by a palladium catalyst.

Atanu Modak1, Togati Naveen, Debabrata Maiti

  • 1Department of Chemistry, Indian Institute of Technology, Powai, Mumbai, 400076, India.

Chemical Communications (Cambridge, England)
|November 21, 2012
PubMed
Summary
This summary is machine-generated.

A novel method for selective dehydroxymethylation was developed using palladium(II) acetate. This approach enables regioselective functionalization by temporarily utilizing the hydroxymethyl group

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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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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions

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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

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Catalysis

Background:

  • Selective functionalization of organic molecules is crucial for complex synthesis.
  • Existing methods for dehydroxymethylation often lack regioselectivity or require harsh conditions.
  • The hydroxymethyl group's properties offer potential for directed chemical transformations.

Purpose of the Study:

  • To develop a general and selective method for dehydroxymethylation.
  • To establish a new synthetic strategy for regioselective functionalization.
  • To leverage the steric, electronic, and coordinating properties of the hydroxymethyl group.

Main Methods:

  • Utilized palladium(II) acetate (Pd(OAc)2) as a catalyst.
  • Employed temporary protection/activation of the hydroxymethyl group.
  • Investigated the regioselectivity of the functionalization reactions.

Main Results:

  • A general method for selective dehydroxymethylation was successfully established.
  • The strategy demonstrated effective regioselective functionalization.
  • Palladium(II) acetate proved to be a versatile and accessible catalyst.

Conclusions:

  • The developed method provides a valuable tool for organic synthesis.
  • Temporary manipulation of the hydroxymethyl group enables precise chemical modifications.
  • This work expands synthetic possibilities in regioselective functionalization.