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Heteropolyacid-Catalyzed Direct Deoxygenation of Propargyl and Allyl Alcohols

Masahiro Egi, Takuya Kawai, Megumi Umemura and Shuji Akai*

*School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka, Shizuoka 422-8526, Japan, Email: akaiu-shizuoka-ken.ac.jp

M. Egi, T. Kawai, M. Umemura, S. Akai, J. Org. Chem., 2012, 77, 7092-7097.

DOI: 10.1021/jo300889p (free Supporting Information)


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Abstract

Proper solvent selection between Cl(CH2)2Cl and CF3CH2OH was the key to high yields in a deoxygenation of propargyl alcohols in the presence of Et3SiH and H3[PW12O40]ĚnH2O as catalyst. Under similar conditions, the deoxygenation of allyl alcohols proceeded to give thermodynamically stable alkenes with migration of the double bonds in good yields.

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Key Words

Deoxygenation, Triethylsilane


ID: J42-Y2012-2700