Palladium-catalyzed cyanation of propargylic carbonates with trimethylsilyl cyanide

Authors
Tsuji, Y Taniguchi, M Yasuda, T Kawamura, T Obora, Y
Citation
Y. Tsuji et al., Palladium-catalyzed cyanation of propargylic carbonates with trimethylsilyl cyanide, ORG LETT, 2(17), 2000, pp. 2635-2637
Citations number
22
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
17
Year of publication
2000
Pages
2635 - 2637
Database
ISI
SICI code
1523-7060(20000824)2:17<2635:PCOPCW>2.0.ZU;2-Q
Abstract
[GRAPHICS] An equimolar mixture of propargylic carbonate (1) and trimethylsilyl cyanid e (2) in THF under reflux affords cyanoallene (3) in the presence of a cata lytic 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 exces s (6 equiv) provides dicyanated products (7 or 8) in high yields.