Palladium-catalyzed intramolecular hydroalkylation of unactivated olefins with dialkyl ketones.
[reaction: see text] Treatment of 3-butenyl heptyl ketone with substoichiometric amounts of PdCl(2)(CH(3)CN)(2) (10 mol %), HCl (0.1 equiv), and CuCl(2) (0.3 equiv) in dioxane at 70 degrees C for 12 h in a sealed tube formed 2-hexylcyclohexanone in 77% isolated yield. A number of alkyl 3-butenyl ketones underwent hydroalkylation under these conditions to form 2-substituted cyclohexanones in moderate to good yield.
Wang
Xiang
X
Duke University, P. M. Gross Chemical Laboratory, Durham, North Carolina 27708-0346, USA.
Pei
Tao
T
Han
Xiaoqing
X
Widenhoefer
Ross A
RA