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Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
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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.
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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.
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Cobalt Catalyzed Reductive Spirocyclopropanation Reactions.

Jacob Werth1, Kristen Berger1, Christopher Uyeda1

  • 1Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907, United States.

Advanced Synthesis & Catalysis
|November 16, 2020
PubMed
Summary

Cobalt pyridine-diimine complexes enable reductive spirocyclopropanation of dienes using zinc carbenoids. This method overcomes limitations of previous Simmons-Smith reactions, enabling complex molecule synthesis.

Keywords:
carbenescarbenoidscobaltcyclopropanesspiro compounds

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Area of Science:

  • Organometallic Chemistry
  • Synthetic Organic Chemistry
  • Catalysis

Background:

  • Simmons-Smith cyclopropanation is a vital synthetic tool.
  • Reactions using zinc carbenoids with beta-hydrogen atoms are often hampered by 1,2-hydride shifts.
  • Development of new catalytic systems is needed to overcome these limitations.

Purpose of the Study:

  • To develop a novel cobalt-catalyzed reductive spirocyclopropanation reaction.
  • To utilize gem-dichlorocycloalkanes as carbene precursors with zinc as the electron source.
  • To demonstrate the utility of the developed catalyst system in complex molecule synthesis.

Main Methods:

  • Catalytic reductive spirocyclopropanation using cobalt pyridine-diimine complexes.
  • Employing gem-dichlorocycloalkanes and zinc as reagents.
  • Utilizing Rh-catalyzed [5 + 2]-cycloaddition for intramolecular reactions.

Main Results:

  • Effective spirocyclopropanation of terminal 1,3-dienes was achieved.
  • The reaction demonstrated broad substrate scope, including sulfur and nitrogen heterocycles.
  • Suppression of the 1,2-hydride shift was observed, a significant improvement over existing methods.
  • Rapid synthesis of a complex tricyclic framework via intramolecular cycloaddition was demonstrated.

Conclusions:

  • Cobalt pyridine-diimine complexes provide an effective catalyst for reductive spirocyclopropanation.
  • This method offers a robust alternative to traditional Simmons-Smith reactions, particularly for challenging substrates.
  • The developed catalytic system facilitates the construction of complex molecular architectures.