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Related Concept Videos

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

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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Catalysis02:50

Catalysis

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The presence of a catalyst affects the rate of a chemical reaction. A catalyst is a substance that can increase the reaction rate without being consumed during the process. A basic comprehension of a catalysts’ role during chemical reactions can be understood from the concept of reaction mechanisms and energy diagrams.
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Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

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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...
14.7K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

2.3K
Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
2.3K
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

4.9K
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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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
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Transition-Metal Hydride Catalysis Meets Nitrenoid Transfer: Design Principles for Precision C-N Bond Formation.

Xiang Lyu1,2, Hoonchul Choi1,2, Sukbok Chang1,2

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Transition-metal hydride catalysis enables C-N bond formation. This study reveals two distinct hydroamidation pathways by controlling the order of hydride delivery and nitrenoid generation, enabling new regioselectivity patterns.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Transition-metal hydride (TMH) catalysis is key for hydroamination, forming C-N bonds from alkenes/alkynes.
  • Conventional TMH hydroamination typically involves hydrometalation followed by nitrogen electrophile coupling, favoring specific regioselectivity (e.g., α-amination).
  • Achieving complementary β-selective amination via TMH catalysis remains a significant challenge.

Purpose of the Study:

  • To explore novel hydroamidation regimes by merging TMH catalysis with nitrenoid transfer chemistry.
  • To uncover two distinct and mechanistically orthogonal hydroamidation pathways.
  • To establish step order as a critical parameter for controlling regioselectivity in TMH-catalyzed hydroamidation.

Main Methods:

  • Utilized bench-stable dioxazolones as acyl nitrenoid precursors.
  • Investigated a canonical TMH manifold where hydrometalation precedes nitrenoid transfer.
  • Studied a transposed manifold initiated by nitrenoid precursor activation, exemplified by NiH catalysis.

Main Results:

  • Established a TMH manifold enabling regioselective hydroamidation with broad scope and functional-group compatibility.
  • Discovered a transposed hydroamidation regime via NiH catalysis, enabling β-selective amination.
  • Achieved previously inaccessible regioselectivity patterns, including β-lactam formation and enantioselective β-amidation.

Conclusions:

  • The order of elementary steps (hydride delivery vs. nitrenoid generation) is a central design principle in TMH-catalyzed hydroamidation.
  • This control allows access to complementary regio- and stereochemical outcomes.
  • The developed framework offers a predictive platform for precision C-N bond construction, extendable to carbene transfer processes.