Indium-Catalyzed Radical Reductions of Organic Halides with Hydrosilanes

Katsukiyo Miura,* Mitsuru Tomita, Yusuke Yamada, and Akira Hosomi*

*Department of Chemistry, 21st Century COE, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan, Email: miurachem.tsukuba.ac.jp, hosomichem.tsukuba.ac.jp

K. Miura, M. Tomita, Y. Yamada, A. Hosomi, J. Org. Chem., 2007, 72, 787-792.

DOI: 10.1021/jo061880o

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Abstract

The In(OAc)₃-catalyzed reaction of bromo- and iodoalkanes with PhSiH₃ in THF at 70 C gave dehalogenated alkanes in good to high yields in the presence of Et₃B and air. 2,6-lutidine as additive enabled an efficient reduction of simple and functionalized iodoalkanes in EtOH. GaCl₃ was found to be an effective catalyst for the reduction of haloalkanes with poly(methylhydrosiloxane).

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proposed mechanism

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Key Words

Phenylsilane, Indium, Dehalogenations

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ID: J42-Y2007-0300