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Triethylsilane-indium(III) chloride system as a radical reagent
Naoki Hayashi1, Ikuya Shibata, Akio Baba
1Department of Molecular Chemistry, Science and Technology Center for Atoms, Molecules and Ions Control (STAMIC), Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.
Organic Letters
|December 21, 2004
Summary
A new method generates indium hydride (Cl2InH) via transmetalation. This approach effectively achieves hydroindation of alkynes in enyne cyclizations, overcoming issues with previous borane-based systems.
Area of Science:
- Organometallic Chemistry
- Synthetic Organic Chemistry
Background:
- Indium hydride (InH3) and its derivatives are valuable reagents in organic synthesis.
- Previous methods for generating indium hydride, such as using NaBH4-InCl3, suffer from side reactions due to coexisting boranes.
Purpose of the Study:
- To develop a novel and efficient method for generating indium hydride (Cl2InH).
- To address the limitations of existing methods in the intramolecular cyclization of enynes.
Main Methods:
- A new generation method for Cl2InH was established through the transmetalation of indium(III) chloride (InCl3) with triethylsilane (Et3SiH).
- The developed system was applied to the intramolecular cyclization of enynes.
Main Results:
- The transmetalation reaction successfully produced Cl2InH.
- The new system effectively performed hydroindation of alkynes.
- The problem of side reactions associated with boranes in previous systems was resolved.
Conclusions:
- The Et3SiH-InCl3 system provides a clean and effective route to Cl2InH.
- This method offers an improved solution for hydroindation in enyne cyclizations, avoiding problematic side reactions.