Selenides, alkenyl coupling reactions

Tetrakis(triphenylphosphine)palladiuin(0)-copper(l) iodide. 18,349-350 20,369 Coupling reactions. a-Fluorovinylstannanes are a source of a-fluorostyrenes by virtue of their capacity of partaking in the Stille coupling. A synthesis of (Z)-alkenes is based on the Pd(0)-catalyzed exchange of alkenyl tellurides or selenides with zinc followed by the Negishi coupling. ... 

The coupling of arylzinc halides with alkyl (E)-2,3-dibromoalkenoates occurs at C-3. 3-Arylindoles are obtained from 3-indolylzinc halides with haloarenes." A synthesis of 1,4-disubstituted butadienes starts from the hydrozirconation of ethynyl phenyl selenide. After Pd(0)-catalyzed coupling with alkenyl bromides, the seleno group is replaced via Grignard reaction in the presence of (Ph3P)2NiCl2. 

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