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An Efficient Protocol for the Stereoselective Construction of Multisubstituted Fluorine-Containing Alkenes. A Palladium-Catalyzed Bisstannylation of Fluorinated Internal Alkynes

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journal contribution
posted on 2009-11-06, 00:00 authored by Tsutomu Konno, Ryoko Kinugawa, Atsunori Morigaki, Takashi Ishihara
On treatment of various fluorinated internal alkynes with 1.2 equiv of hexabutylditin under the influence of 2.5 mol % of Pd(t-BuNC)2Cl2 in THF at room temperature for 4 h, the bisstannylation proceeded smoothly to afford the corresponding bisstannylated cis-adducts in high yields. Thus obtained adducts were subjected to the Stille cross-coupling reaction to give the corresponding tetrasubstituted fluorine-containing alkenes with defined stereochemistry in good yields.