Palladium-Catalyzed Cyanation of Propargylic Carbonates with Trimethylsilyl Cyanide
journal contributionposted on 2000-07-28, 00:00 authored by Yasushi Tsuji, Masahiko Taniguchi, Tamami Yasuda, Takashi Kawamura, Yasushi Obora
An equimolar mixture of propargylic carbonate (1) and trimethylsilyl cyanide (2) in THF under reflux affords cyanoallene (3) in the presence of a catalytic amount (5 mol %) of Pd(PPh3)4. In the reaction, the trimethylsilyl moiety of 2 effectively traps the leaving group of 1. The use of 2 in excess (6 equiv) provides dicyanated products (7 or 8) in high yields.