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Palladium-Catalyzed Cyanation of Propargylic Carbonates with Trimethylsilyl Cyanide

Yasushi Tsuji, Masahiko Taniguchi, Tamami Yasuda, Takashi Kawamura and Yasushi Obora

*Catalysis Research Center and Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0811, Japan

Y. Tsuji, M. Taniguchi, T. Yasuda, T. Kawamura, Y. Obora, Org. Lett., 2000, 2, 2635-2637.

DOI: 10.1021/ol006160x (free Supporting Information)


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Abstract

Pd(PPh3)4 catalyzes a cyanation of propargylic carbonates with trimethylsilyl cyanide in THF under reflux to afford cyanoallenes. The use of trimethylsilyl cyanide in excess (6 equiv) provides dicyanated products in high yields.

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Key Words

cyanation, allenes


ID: J54-Y2000