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Related Experiment Videos

Efficient medium-ring cyclization under non-high-dilution conditions using SmI 2.

Hiroaki Tamiya1, Kazuhiro Goto, Fuyuhiko Matsuda

  • 1Division of Material Science, Graduate School of Environmental Earth Science, Hokkaido University, Sapporo 060-0810, Japan. fmatsuda@ees.hokudai.ac.jp

Organic Letters
|February 14, 2004
PubMed
Summary

A new SmI(2)-mediated Barbier-type coupling method efficiently creates medium-sized rings. This simple protocol yields valuable carbocycles and heterocycles in high amounts without requiring high dilution.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • The synthesis of medium-sized rings (eight- to nine-membered) is challenging due to entropic and enthalpic factors.
  • Traditional methods often require high-dilution conditions, increasing experimental complexity and cost.
  • Efficient access to carbocyclic and heterocyclic medium rings is crucial for drug discovery and materials science.

Purpose of the Study:

  • To develop a general, efficient, and simple method for synthesizing medium-sized rings.
  • To explore the utility of samarium(II) iodide (SmI(2))-mediated Barbier-type coupling for ring formation.
  • To demonstrate the applicability of the protocol to both carbocycles and heterocycles.

Main Methods:

  • Utilized samarium(II) iodide (SmI(2)) as a reducing agent for Barbier-type coupling reactions.

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  • Employed a general protocol applicable to various substrates for medium ring construction.
  • Performed reactions without the need for high-dilution techniques.

    • Main Results:

    • Successfully synthesized various eight- and nine-membered carbocycles and heterocycles.
    • Achieved high efficiency and yields, often near quantitative.
    • Demonstrated that the protocol is experimentally simple and does not require specialized conditions.

    Conclusions:

    • A novel and practical SmI(2)-mediated Barbier-type coupling method for medium ring synthesis has been established.
    • This protocol provides efficient access to frequently inaccessible medium-sized carbocycles and heterocycles.
    • The method's simplicity and high yields offer significant advantages for synthetic chemists.