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InCl3/I2-Catalyzed Cross-Coupling of Alkyl Trimethylsilyl Ethers and Allylsilanes via an in Situ Derived Combined Lewis Acid of InCl3 and Me3SiI

Takahiro Saito, Yoshihiro Nishimoto, Makoto Yasuda and Akio Baba*

*Department of Applied Chemistry, Center for Atomic and Molecular Technologies (CAMT), Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan, Email: babachem.eng.osaka-u.ac.jp

T. Saito, Y. Nishimoto, M. Yasuda, A. Baba, J. Org. Chem., 2007, 72, 8588-8590.

DOI: 10.1021/jo7015289


Abstract

Direct Csp3-Csp3 coupling of various aliphatic trimethylsilyl ethers and allylsilanes is effectively catalyzed by InCl3 and I2. The transformation probably involves an in situ-derived combined Lewis acid of InCl3 and Me3SiI. The reaction allows the construction of quaternary-quaternary and quaternary-tertiary carbon-carbon bonds and tolerates aryl halide moieties.

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Key Words

Allylation


ID: J42-Y2007-3480