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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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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A hydrogen bond is formed when a weakly positive hydrogen atom already bonded to one electronegative atom (for example, the oxygen in the water molecule) is attracted to another electronegative atom from another polar molecule, such as water (H2O), hydrogen fluoride (HF), or ammonia (NH3). The huge electronegativity difference between the H atom (2.1) and the atom to which it is bonded (4.0 for an F atom, 3.5 for an O atom, or 3.0 for an N atom), combined with the very small size of an H atom...
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Synthesis of Metal Nanoparticles Supported on Carbon Nanotube with Doped Co and N Atoms and its Catalytic Applications in Hydrogen Production
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New Architectures in Hydrogen Bond Catalysis.

Andrew A Rodriguez1, Hoseong Yoo, Joseph W Ziller

  • 1Department of Chemistry, University of California, Irvine, Irvine, CA 92697-2025, USA.

Tetrahedron Letters
|February 18, 2010
PubMed
Summary

New achiral sulfamide, phosphoric triamide, and thiophosphoric triamide compounds show promising catalytic activity. These novel hydrogen bond catalysts are effective in Friedel-Crafts and Baylis-Hillman reactions, rivaling established thiourea catalysts.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Crystallography

Background:

  • Hydrogen bond catalysis is crucial for various organic transformations.
  • Thiourea derivatives are known effective hydrogen bond catalysts.
  • Exploring novel catalyst scaffolds is essential for advancing synthetic methodologies.

Purpose of the Study:

  • To synthesize and characterize new achiral sulfamide, phosphoric triamide, and thiophosphoric triamide compounds.
  • To evaluate the catalytic performance of these novel compounds in Friedel-Crafts and Baylis-Hillman reactions.
  • To elucidate the solid-state structures of the synthesized compounds using X-ray crystallography.

Main Methods:

  • Synthesis of achiral sulfamide, phosphoric triamide, and thiophosphoric triamide derivatives.
  • Catalytic activity assessment in Friedel-Crafts and Baylis-Hillman reactions.
  • X-ray crystallography for structural determination.

Main Results:

  • Successful synthesis of novel achiral sulfamide, phosphoric triamide, and thiophosphoric triamide compounds.
  • Demonstrated favorable catalytic activity in Friedel-Crafts and Baylis-Hillman reactions, comparable to thiourea catalysts.
  • Detailed description of the solid-state structures obtained through X-ray crystallography.

Conclusions:

  • The newly synthesized achiral sulfamide, phosphoric triamide, and thiophosphoric triamide compounds represent a new class of effective hydrogen bond catalysts.
  • These compounds offer a viable alternative to existing thiourea catalysts for specific organic reactions.
  • Structural insights from X-ray crystallography aid in understanding their catalytic mechanisms.