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Related Concept Videos

Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)01:20

Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)

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Two NMR-active nuclei bonded to a central atom can be involved in geminal or two-bond coupling. Geminal coupling is commonly seen between diastereotopic protons in chiral molecules and unsymmetrical alkenes, among others.
The central atom need not be NMR-active because its electrons are affected by the electron polarization of the spin-active atoms. However, spin information is transmitted less effectively than in one-bond coupling, and 2J values are usually weaker than 1J values. The energy of...
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Crossed Aldol Reactions: Overview01:04

Crossed Aldol Reactions: Overview

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Crossed aldol addition is the reaction between two different carbonyl compounds under acidic or basic conditions. Here, both the carbonyl compounds function as nucleophiles and electrophiles. As shown in Figure 1, such a reaction yields a mixture of products, two of which are formed via self-condensation, while the remaining two are formed via crossed-condensation. Without adjustment, the reaction's usefulness in organic chemistry is decreased.
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

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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

1.9K
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.
1.9K
β-Dicarbonyl Compounds via Crossed Claisen Condensations01:18

β-Dicarbonyl Compounds via Crossed Claisen Condensations

3.1K
Crossed Claisen condensations are base-promoted reactions between two different ester molecules producing β-dicarbonyl compounds.  The reaction involving esters, with both containing α hydrogen, results in a mixture of four different products that are difficult to isolate. This reduces the synthetic utility of the reaction.
3.1K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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3.3K
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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Updated: Jul 16, 2025

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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Geminal-atom catalysis for cross-coupling.

Xiao Hai1, Yang Zheng1, Qi Yu2,3

  • 1Department of Chemistry, National University of Singapore, Singapore, Singapore.

Nature
|September 21, 2023
PubMed
Summary
This summary is machine-generated.

Geminal-atom catalysts (GACs) pair single atoms for enhanced organic synthesis. These novel catalysts enable efficient C-X cross-couplings and complex molecule assembly, overcoming limitations of single-atom catalysts.

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Area of Science:

  • Heterogeneous catalysis
  • Materials science
  • Organic synthesis

Background:

  • Single-atom catalysts (SACs) offer well-defined active sites but have limitations in complex transformations due to restricted environments.
  • The spatial arrangement and electronic states of mononuclear metal species in SACs may hinder optimal catalytic activity.

Purpose of the Study:

  • To introduce a novel class of heterogeneous geminal-atom catalysts (GACs) that pair single-atom sites in close proximity.
  • To demonstrate the enhanced catalytic performance of GACs for diverse C-X cross-coupling reactions.

Main Methods:

  • Synthesis of GACs using a polymeric carbon nitride (PCN) host with nitrogen anchoring groups for Cu coordination.
  • In situ characterization and quantum-theoretical studies to elucidate reaction mechanisms.
  • Testing GACs in various C-X (X = C, N, O, S) cross-coupling reactions.

Main Results:

  • GACs exhibit a specific coordination and spatial proximity of Cu atoms (~4 Å separation) at high metal density.
  • A cooperative bridge-coupling pathway facilitated by dynamic Cu-Cu bonding enables efficient cross-couplings with low activation barriers.
  • GACs demonstrate high activity and selectivity in synthesizing complex heterocycles, sterically hindered molecules, and pharmaceuticals.

Conclusions:

  • Geminal-atom catalysts represent a significant advancement over SACs for complex organic synthesis.
  • The unique cooperative mechanism in GACs prevents homo-coupling and promotes diverse cross-coupling reactions.
  • GACs show broad applicability for fine chemical manufacturing, including scale-up and continuous flow processes.