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Related Experiment Videos

Atom transfer cyclization catalyzed by InCl3 via halogen activation.

Gregory R Cook1, Ryuji Hayashi

  • 1Department of Chemistry and Molecular Biology, North Dakota State University, Fargo, North Dakota 58105-5516, USA. Gregory.Cook@ndsu.edu

Organic Letters
|March 10, 2006
PubMed
Summary

Indium trichloride efficiently catalyzes allylic halide and alkyne cyclization via atom transfer. This Lewis acid catalysis pathway yields cyclization products by transferring halogen atoms from substrates or solvents.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Reaction Mechanisms

Background:

  • Allylic halides and alkynes are versatile building blocks in organic synthesis.
  • Atom transfer reactions offer unique pathways for forming cyclic structures.
  • Efficient catalytic systems are crucial for developing sustainable synthetic methodologies.

Purpose of the Study:

  • To investigate the catalytic activity of indium trichloride in cyclization reactions.
  • To elucidate the reaction mechanism of allylic halide and alkyne cyclization with atom transfer.
  • To explore the scope and limitations of this transformation with varying alkyne substrates.

Main Methods:

  • Cyclization reactions were performed using allylic halides and alkynes in the presence of indium trichloride as a catalyst.

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  • Methylene chloride was employed as the solvent.
  • Mechanistic studies were conducted to support the proposed reaction pathway.

    • Main Results:

    • Indium trichloride demonstrated high efficiency as a catalyst for the atom transfer cyclization of allylic halides and alkynes.
    • Mechanistic investigations indicated a cationic reaction pathway initiated by Lewis acid activation of the allylic halogen.
    • The reaction yielded cyclization products with concomitant halogen atom transfer, originating from either the allylic halide substrate or the methylene chloride solvent, depending on the alkyne substitution.

    Conclusions:

    • Indium trichloride is an effective catalyst for atom transfer cyclization reactions involving allylic halides and alkynes.
    • The reaction proceeds through a cationic mechanism involving Lewis acid activation and nucleophilic attack.
    • This methodology provides a novel route to functionalized cyclic compounds with tunable halogen incorporation.