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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 (free Supporting Information)


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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, Reduction of Alkynes, Dehalogenations


ID: J54-Y2004-1240