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Sequential silylcarbocyclization/silicon-based cross-coupling reactions.

Scott E Denmark1, Jack Hung-Chang Liu

  • 1Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA. denmark@scs.uiuc.edu

Journal of the American Chemical Society
|March 6, 2007
PubMed
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A new rhodium-catalyzed silylcarbocyclization followed by palladium-catalyzed cross-coupling efficiently synthesizes highly substituted cyclopentanes. This method creates complex cyclic structures with excellent control and broad compatibility.

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Cyclopentane scaffolds are prevalent in natural products and pharmaceuticals.
  • Efficient and versatile synthetic routes to highly substituted cyclopentanes are highly sought after.
  • Existing methods often lack broad substrate scope or require harsh conditions.

Purpose of the Study:

  • To develop a novel sequential catalytic strategy for synthesizing highly substituted cyclopentanes.
  • To combine rhodium-catalyzed silylcarbocyclization with palladium-catalyzed cross-coupling.
  • To establish a versatile method with broad functional group tolerance.

Main Methods:

  • Sequential reaction involving rhodium-catalyzed silylcarbocyclization of 1,6-enynes with benzyldimethylsilane.

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  • Palladium-catalyzed cross-coupling of the resulting alkylidenesilanes using tetra-n-butylammonium fluoride.
  • Exploration of various substitution patterns and heteroatom incorporation.

    • Main Results:

    • Successful synthesis of densely functionalized 3-(Z)-benzylidenecyclopentanes and heterocycles.
    • High yields and complete retention of double bond configuration achieved under mild conditions.
    • Broad substrate scope demonstrated, compatible with diverse substitution patterns and heteroatoms.

    Conclusions:

    • A robust and efficient sequential catalytic system for cyclopentane synthesis has been established.
    • The developed methodology offers a versatile platform for accessing complex cyclic structures.
    • This approach provides a valuable tool for organic synthesis and drug discovery.