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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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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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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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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.
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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

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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.
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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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Iron-catalyzed alkene isomerization and tandem functionalization.

Rohit Kumar1,2, Anirban Sen1,2, Tanuja Tewari1,2

  • 1Polymer Science and Engineering Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune, India.

Communications Chemistry
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Summary

This study introduces an iron catalyst for efficient alkene isomerization, replacing expensive noble metals. This earth-abundant catalyst enables mild conditions and further functionalization into aldehydes.

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Area of Science:

  • Catalysis
  • Organometallic Chemistry
  • Sustainable Chemistry

Background:

  • Alkene isomerization is crucial for synthesizing internal alkenes.
  • Noble metal catalysts are effective but costly and scarce.
  • Earth-abundant alternatives are sought for sustainable catalysis.

Purpose of the Study:

  • To develop an efficient iron-catalyzed method for alkene isomerization.
  • To replace expensive noble metal catalysts with an earth-abundant alternative.
  • To explore tandem reactions for further functionalization of alkenes.

Main Methods:

  • Synthesis of a mononuclear Fe(II) complex, [HFe(CO)4SiPh3] ([Fe-1]).
  • Catalytic isomerization of terminal alkenes to internal alkenes under solvent-free conditions.
  • Kinetic studies to determine reaction order and rate.
  • Tandem reactions including isomerizing-ozonolysis and isomerizing-hydroformylation.

Main Results:

  • The Fe(II) complex efficiently catalyzes alkene isomerization under mild, solvent-free conditions.
  • Gram-scale reactions demonstrated the synthetic utility and scalability.
  • Kinetic analysis showed approximately first-order kinetics with a rate of 7.08 × 10-3 Mmin-1.
  • Successful tandem functionalization to aldehyde products was achieved.

Conclusions:

  • Iron-based catalysts offer a cost-effective and sustainable alternative for alkene isomerization.
  • The developed Fe(II) catalyst demonstrates high efficiency and broad applicability.
  • The methodology allows for sequential functionalization, expanding synthetic possibilities.