Palladium-catalyzed cyanation of propargylic carbonates with trimethylsilyl cyanide
[reaction: see text]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.
Tsuji
Y
Catalysis Research Center and Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo, Japan. tsuji@cat.hokudai.ac.jp
Taniguchi
M
Yasuda
T
Kawamura
T
Obora
Y