In the presence of CuCl, zirconacyclopentanes reacted with two equivalents of a propargyl halide to give bisallenylation products in moderate to high yields. By controlling the amount of CuCl, stepwise allenylation was achieved and a variety of unsymmetrically substituted diallene derivatives were prepared as well.
propargyl electrophile - zirconacyclopentane - allene - SN2′ reaction - copper(I) chloride