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Synthesis 2005(12): 2055-2060  
DOI: 10.1055/s-2005-870017
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York

Diallene Formation by Copper(I)-Mediated Reactions of Zirconacyclo­pentanes with Propargyl Halides

Zheng Duana,b, Takahiro Nishimotoa,b, Masamichi Ogasawaraa,b, Tamotsu Takahashi*a,b
a Catalysis Research Center and Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita-ku, Sapporo 001-0021, Japan
b SORST, Japan Science and Technology Agency (JST), Kita-ku, Sapporo 001-0021, Japan
Fax: +81(11)7069150; e-Mail: tamotsu@cat.hokudai.ac.jp;
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Publication History

Received 14 February 2005
Publication Date:
07 July 2005 (online)

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Abstract

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.

Key words

propargyl electrophile - zirconacyclopentane - allene - SN2′ reaction - copper(I) chloride

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