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Platinum-Catalyzed Nucleophilic Addition of Vinylsilanes at the β-Position

Katsukiyo Miura*, Gen Inoue, Hisashi Sasagawa, Hidenori Kinoshita, Junji Ichikawa and Akira Hosomi

*Department of Applied Chemistry, Graduate School of Science and Engineering, Saitama University, Sakura-ku, Saitama 338-8570, Japan, Email: kmiuraapc.saitama-u.ac.jp

K. Miura, G. Inoue, H. Sasagawa, H. Kinoshita, J. Ichikawa, A. Hosomi, Org. Lett., 2009, 11, 5066-5069.

DOI: 10.1021/ol902060r (free Supporting Information)


Abstract

In the presence of catalytic amounts of PtCl2 and metal iodides, β-substituted vinylsilanes reacted with aldehydes at the β-position to give allyl silyl ethers. Addition to aromatic aldehydes proceeded efficiently in the presence of LiI whereas MnI2 was found to be effective in addition to aliphatic aldehydes.

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Key Words

Allylic Alcohols, Silyl Ethers


ID: J54-Y2009-3330