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Esters to Alcohols: Hydride Reductions01:17

Esters to Alcohols: Hydride Reductions

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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,...
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Nitriles to Amines: LiAlH4 Reduction00:55

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Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
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Alcohols from Carbonyl Compounds: Reduction02:23

Alcohols from Carbonyl Compounds: Reduction

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Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...
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Radical Oxidation of Allylic and Benzylic Alcohols01:21

Radical Oxidation of Allylic and Benzylic Alcohols

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Activated manganese(IV) oxide can selectively oxidize allylic and benzylic alcohols via a radical intermediate mechanism. Primary allylic alcohols are oxidized to aldehydes, while secondary allylic alcohols yield ketones. The redox reaction of potassium permanganate with an Mn(II) salt such as manganese sulfate (under either alkaline or acidic conditions), followed by thorough drying, yields the oxidizing agent: activated MnO2. While MnO2 is insoluble in the solvents used for the reaction, the...
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Amides to Amines: LiAlH4 Reduction01:20

Amides to Amines: LiAlH4 Reduction

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Amide reduction with strong reducing agents like lithium aluminum hydride proceeds through a nucleophilic acyl substitution to form amines. Primary, secondary, and tertiary amides yield primary, secondary, and tertiary amines, respectively.
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.
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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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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
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Redox-active ligand based Mn(I)-catalyst for hydrosilylative ester reduction.

Soumi Chakraborty1, Arpan Das1, Swadhin K Mandal1

  • 1Department of Chemical Sciences, Indian Institute of Science Education and Research (IISER) Kolkata, Mohanpur Campus, Pin-741246, Nadia, West Bengal, India. swadhin.mandal@iiserkol.ac.in.

Chemical Communications (Cambridge, England)
|November 15, 2021
PubMed
Summary

A novel manganese(I) catalyst with a redox-active phenalenyl ligand efficiently converts esters to alcohols using polymethylhydrosiloxane. Ligand-metal cooperation and single electron transfer initiate the catalytic cycle via Si-H bond activation.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Green Chemistry

Background:

  • Hydrosilylation is a key transformation in organic synthesis.
  • Developing efficient and sustainable catalytic systems for ester reduction is crucial.
  • Polymethylhydrosiloxane (PMHS) offers an inexpensive and practical silicon source.

Purpose of the Study:

  • To report a new manganese(I) catalyst for ester hydrosilylation.
  • To utilize a redox-active phenalenyl (PLY) ligand for enhanced catalytic activity.
  • To achieve efficient reduction of esters to alcohols under mild conditions.

Main Methods:

  • Synthesis and characterization of a Mn(I) complex with a PLY ligand.
  • Catalytic testing for the hydrosilylation of various esters using PMHS.
  • Mechanistic studies including kinetic and spectroscopic analyses.

Main Results:

  • The Mn(I)-PLY catalyst demonstrated high efficiency in ester to alcohol conversion.
  • The reaction proceeded under mild conditions with PMHS as the reductant.
  • Mechanistic studies revealed a ligand-metal cooperation mechanism involving single electron transfer (SET).

Conclusions:

  • A novel and efficient Mn(I) catalyst for ester hydrosilylation has been developed.
  • The catalyst's activity is attributed to ligand-metal cooperation and SET-initiated Si-H bond activation.
  • This work offers a sustainable route for alcohol synthesis from esters.