Synlett

Hg (OTf) 2-Catalyzed Instantaneous Hydration of β-and δ-Hydroxy Internal Alkynes with Complete Regioselectivity

M Nishizawa, T Takemoto, I Sasaki, M Nakano, E Ho…

Index: Nishizawa, Mugio; Takemoto, Takayuki; Sasaki, Ikuo; Nakano, Mayo; Ho, Elisabeth; Namba, Kosuke; Yamamoto, Hirofumi; Imagawa, Hiroshi Synlett, 2009 , # 7 p. 1175 - 1179

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Abstract

Abstract The hydration of β-and δ-hydroxy internal alkynes catalyzed by Hg (OTf) 2 took place instantaneously to give ketones with complete regioselectivity under mild conditions, whereas the hydration of internal alkyne without hydroxy moiety was very slow and gave a mixture of ketones. If the hydroxy group is located more than five carbons from the triple bond it has no significant effect upon the hydration reaction.