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ChemInform Abstract

Stille coupling of dibromoalkenes of type (I) with organostannanes leads to (Z)-monobromides like (III) in good to high yields when the reaction is run in low to nonpolar solvents with the ligand P(o-Fur)₃. This coupling is less suitable for 2-aryl-1,1-dibromoalkenes bearing strongly electron donating substituents at ortho or para positions. It can be applied to the stereospecific synthesis of trisubstituted alkenes. Stille coupling of (I) in a higher polar solvent gives internal alkynes like (VIII) in high yields. This represents a new, general, and mild approach to internal alkynes.