Triethylsilane-Indium(III) Chloride System as a Radical Reagent

Naoki Hayashi, Ikuya Shibata and Akio Baba*

*Department 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, Email: babachem.eng.osaka-u.ac.jp

N. Hayashi, I. Shibata, A. Baba, Org. Lett., 2004, 6, 4981-4983.

DOI: 10.1021/ol047849v

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Abstract

Indium hydride (Cl₂InH) was generated by the transmetalation of InCl₃ with Et₃SiH. In the previously reported system (NaBH₄-InCl₃), the coexistent borane can cause side reactions. The use of Et₃SiH instead of NaBH₄ affords effective hydroindation of alkynes.

Indium hydride generated from readily available Et₃SiH and InCl₃ offers mild conditions and low toxicity, and is therefore a promising alternative to Bu₃SnH.

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Key Words

Indium hydride, Triethylsilane, Semireduction of Alkynes, Dehalogenations

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ID: J54-Y2004-1240