Convenient and Efficient Access to Fluoroalkylated Vinylphosphonates via Highly Regio- and Stereoselective Hydrometalation or Carbometalation Reactions of Fluorine-Containing Alkynylphosphonates

Tsutomu Konno; Atsunori Morigaki; Kazuo Ninomiya; Tomotsugu Miyabe; Takashi Ishihara

doi:10.1055/s-2008-1032143

PAPER

Convenient and Efficient Access to Fluoroalkylated Vinylphosphonates via Highly Regio- and Stereoselective Hydrometalation or Carbometalation Reactions of Fluorine-Containing Alkynylphosphonates

Tsutomu Konno*, Atsunori Morigaki, Kazuo Ninomiya, Tomotsugu Miyabe, Takashi Ishihara
Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan
Fax: +81(75)7247580; e-Mail: konno@chem.kit.ac.jp;

Abstract

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Abstract

The hydrostannation, carbocupration, and carbozincation reactions of fluorinated alkynylphosphonates were investigated. The hydrostannation reaction proceeded smoothly without an additive (e.g., BEt₃/O₂, AIBN) to give the corresponding vinylstannanes in a highly regio- and stereoselective manner. Various cuprates, prepared from organolithium, Grignard, and organozinc reagents, could participate nicely in the carbocupration reactions, the corresponding adducts were obtained in good to high yields. Dialkylzinc reagents reacted smoothly with the alkynylphosphonates even in the absence of copper salt to afford the corresponding adducts in good yields.

Key words

fluoroalkenes - alkynylphosphonates - hydrostannation - carbocupration - carbozincation - regioselective - stereoselective

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