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Paper | Special issue | Vol 103, No. 2, 2021, pp.769-777
Published online, 22nd October, 2020
DOI: 10.3987/COM-20-S(K)36
Preparation of 2-Aryl-3-silyl- and 2-Aryl-3-germyl-1,3-butadienes via Arylnickelation and Zinciomethylation

Nana Yoshino, Betemariam Sharewa, Zenichi Ikeda, and Seijiro Matsubara*

*Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-Katsura, Nishikyo, Kyoto 615-8510, Japan

Abstract

Benzyl 3-silyl(or germyl)propargyl ether, aryl iodide, and bis(iodozincio)methane were assembled in the presence of a nickel catalyst to efficiently give 2-aryl-3-silyl(germyl)-1,3-butadienes via arylnickelation, zinciomethylation, and 1,4-elimination of zinc benzyloxide. As a ligand, an electron-deficient phospine such as tris(2-furyl)phosphine was effective.