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Related Concept Videos

Catalysis02:50

Catalysis

29.9K
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: 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

8.8K
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.
8.8K
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

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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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Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

13.8K
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...
13.8K
Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

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Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

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Efficient C-H Amination Catalysis Using Nickel-Dipyrrin Complexes.

Yuyang Dong1, Ryan M Clarke1, Gerard J Porter1

  • 1Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, United States.

Journal of the American Chemical Society
|May 29, 2020
PubMed
Summary
This summary is machine-generated.

A novel nickel catalyst enables efficient intramolecular C-H amination of aliphatic azides at room temperature. This reaction proceeds via a rate-determining hydrogen atom abstraction step, forming N-heterocycles with broad substrate scope and functional group tolerance.

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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Organic Synthesis

Background:

  • Intramolecular C-H amination is a crucial transformation for synthesizing N-heterocycles.
  • Developing mild and efficient catalytic systems for C-H functionalization remains a significant challenge.
  • Nickel catalysis offers a promising avenue for activating inert C-H bonds.

Purpose of the Study:

  • To develop a novel nickel catalyst for intramolecular C-H amination using aliphatic azides.
  • To investigate the scope, chemoselectivity, and functional group tolerance of the catalytic system.
  • To elucidate the reaction mechanism, including the rate-determining step and catalytic resting state.

Main Methods:

  • Synthesis and characterization of a dipyrrin-supported nickel catalyst.
  • Exploration of substrate scope for C-H amination, including various C-H bond types and functional groups.
  • Mechanistic studies using Nuclear Magnetic Resonance (NMR) spectroscopy, kinetic isotope effect (KIE) measurements, and Eyring analysis.

Main Results:

  • The (AdFL)Ni(py) catalyst efficiently promotes intramolecular C-H amination of aliphatic azides under mild conditions (room temperature, 0.1-2 mol% loading).
  • The reaction exhibits broad substrate scope, successfully aminating benzylic, tertiary, secondary, and primary C-H bonds with high chemoselectivity for weaker C-H bonds.
  • Mechanistic investigations reveal a rate-determining hydrogen atom abstraction step, likely involving H-atom tunneling, with the catalyst's resting state identified as a nickel iminyl radical.

Conclusions:

  • A highly effective nickel catalyst for intramolecular C-H amination has been developed, enabling the synthesis of N-heterocycles.
  • The reaction proceeds under mild conditions and demonstrates excellent functional group tolerance and chemoselectivity.
  • The mechanistic studies provide critical insights into the catalytic cycle, highlighting the importance of hydrogen atom abstraction and tunneling.