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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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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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Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

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By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
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Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

3.0K
Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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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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Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

14.7K
Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Iron-Catalyzed C-H Functionalization Processes.

Gianpiero Cera1, Lutz Ackermann2

  • 1Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstr. 2, 37077, Göttingen, Germany.

Topics in Current Chemistry (Cham)
|August 31, 2016
PubMed
Summary
This summary is machine-generated.

Iron catalysis enables efficient C-H bond transformations. Recent advances in low-valent iron catalysts offer new strategies for C-H activation, leveraging chelation assistance for step-economical reactions.

Keywords:
AlkenylationAlkylationAminationArylationChelation assistanceC–H activationIron

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Synthetic Organic Chemistry

Background:

  • C-H activation is a key transformation in organic synthesis.
  • Iron catalysis is emerging as a sustainable alternative to precious metal catalysis.
  • Low-valent iron complexes enable novel reactivity in C-H activation.

Purpose of the Study:

  • To summarize the recent advancements in iron-catalyzed C-H activation.
  • To highlight the role of low-valent iron in novel C-H activation strategies.
  • To provide an overview of iron catalysis in C-H activation up to May 2016.

Main Methods:

  • Review of literature on iron-catalyzed C-H activation reactions.
  • Focus on chelation-assisted C-H activation strategies.
  • Analysis of the scope and limitations of iron catalysis in C-H functionalization.

Main Results:

  • Iron catalysis provides a cost-effective and sustainable approach to C-H activation.
  • Low-valent iron catalysts facilitate novel C-H activation pathways.
  • Chelation assistance is crucial for directing iron-catalyzed C-H activation.

Conclusions:

  • Iron catalysis is a powerful and versatile tool for C-H bond functionalization.
  • The development of low-valent iron catalysts has expanded the scope of C-H activation.
  • Iron catalysis represents a promising direction for future synthetic methodology.