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Platinum-Catalyzed One-Pot Alkenylation of Aldehydes Using Alkynes and Triethylsilane: Dual Catalysis by Platinum(II) Chloride

Hidenori Kinoshita, Ryousuke Uemura, Daiki Fukuda and Katsukiyo Miura*

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

H. Kinoshita, R. Uemura, D. Fukuda, K. Miura, Org. Lett., 2013, 15, 5538-5541.

DOI: 10.1021/ol4026952 (free Supporting Information)


Abstract

PtCl2 plays a dual role as hydrosilylation and alkenylation catalysts in a one-pot hydrosilylation of terminal alkynes with triethylsilane and subsequent alkenylation of aldehydes with the resultant (E)-alkenylsilanes. The latter alkenylation step proceeds smoothly in the presence of p-benzoquinone and LiI to give allyl silyl ethers in good yields. This one-pot alkenylation tolerates a reasonable range of functional groups.


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Key Words

allylic alcohols


ID: J54-Y2013