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Related Concept Videos

Radical Oxidation of Allylic and Benzylic Alcohols01:21

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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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Wolff–Kishner reduction involves converting aldehydes and ketones to alkanes using hydrazine and a base. The reaction converts a carbonyl group to a methylene group. The method was independently discovered by N. Kishner in 1911 and L. Wolff in 1912. The reduction is carried out in high-boiling solvents such as ethylene glycol and diethylene glycol because heat is required to deprotonate the N–H proton in one of the reaction steps.                                       ...
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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.
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Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate02:21

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Alkenes can be dihydroxylated using potassium permanganate.  The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.
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Acid Halides to Ketones: Gilman Reagent01:14

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Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen...
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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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Solvent-Assisted Ketone Reduction by a Homogeneous Mn Catalyst.

Annika M Krieger1, Vivek Sinha1, Guanna Li2,3

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Organometallics
|August 1, 2022
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Solvent molecules facilitate a novel Meerwein-Ponndorf-Verley (MPV) mechanism in manganese-catalyzed ketone reduction. This pathway, occurring outside the metal center, maintains enantioselectivity, offering new insights for homogeneous catalysis.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Computational Chemistry

Background:

  • Solvent choice and reaction conditions critically influence homogeneous catalytic systems.
  • Understanding reaction mechanisms is key to optimizing catalyst activity and selectivity.
  • Manganese-based catalysts are increasingly explored for transfer hydrogenation reactions.

Purpose of the Study:

  • To investigate the role of solvation in the mechanism of ketone reduction using a Mn-diamine catalyst.
  • To explore a potential Meerwein-Ponndorf-Verley (MPV) pathway in Mn-catalyzed transfer hydrogenation.
  • To determine if this alternative mechanism retains enantioselectivity.

Main Methods:

  • Density functional theory (DFT) calculations.
  • Microsolvated environment modeling with explicit solvent.
  • Ab initio molecular dynamics (AIMD) simulations for key steps.

Main Results:

  • A Meerwein-Ponndorf-Verley (MPV) type mechanism was identified for ketone reduction.
  • This MPV pathway does not involve transition-metal hydride species.
  • Solvent molecules significantly facilitate the MPV mechanism.
  • The MPV pathway retains enantioselectivity imparted by the chiral ligand.

Conclusions:

  • Solvation plays a crucial role in enabling non-traditional reaction pathways like the MPV mechanism in Mn-catalyzed transfer hydrogenation.
  • The identified MPV pathway offers a new perspective on Mn-based homogeneous catalysis.
  • This mechanism's ability to maintain enantioselectivity broadens its potential applicability.