Decarbopalladation of π-Allylpalladium Intermediates Formed from Palladium-Catalyzed Arylations of 3-Allen-1-ols
2002; American Chemical Society; Volume: 4; Issue: 19 Linguagem: Inglês
10.1021/ol026659m
ISSN1523-7060
AutoresChang Ho Oh, Seung‐Hyun Jung, Su Youn Bang, Dai In Park,
Tópico(s)Catalytic Alkyne Reactions
Resumo[reaction: see text] Unusual palladium-catalyzed arylative fragmentations of acyclic 3-allen-1-ols were observed. Oxidative addition of Pd(0) to aryl halides would form the arylpalladium halides, which added to the central carbon of allenes via carbopalladation to form the pi-allylpalladium intermediates. The pi-allylpalladium intermediates would be reductively eliminated via carbon-carbon cleavage to give the arylated dienes and the alpha-hydroxyalkylpalladium intermediates, which were further reductively eliminated to the corresponding aldehydes.
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