The steric course of the palladium promoted amination of simple olefins

✍ Scribed by Björn Åkermark; Jan E. Bäckvall; Kirsti Siirala-Hanseń; Kjell Sjöberg; Krister Zetterberg

• Book ID: 104234820
• Publisher: Elsevier Science
• Year: 1974
• Tongue: French
• Weight: 180 KB
• Volume: 15
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)82490-4

✦ Synopsis

A wide variety of nucleophiles have been observed to add to olefins complexed to palladium.

2

When the nucleophile, e.g. acetate, is added externally trana-addition appears to take place. 2,3.4,5 With aryl-and alkylpalladium compounds, where the aryl and alkyl groups are essentially covalently bound to palladium, &r-addition occurs. 5 Chloride ion, which is more strongly co-ordinated to palladium than acetate, appears to add partially &is5 and the same may be true for hydroxyl. 5

We have recently shown that amines add to double bonds in high yields in an efficient palladiusrpromoted reaction.

In this reaction the olefins show a reactivity pattern similar to that observed for olefins in cycloaddition reactions, e.g. trans-olefins are more reactive than 697 the corresponding cis-olefins and cyclopentene is considerably more reactive than cyclohexene.