I have a reference that uses Pd acetate with the benzo, and some mineral acid H2SO4, HNO3 or HClO4 what is said to make the rxn 50 times faster. HCl inhibites the rxn and PdCl2 doesn't work too much, best catalysts are Pd(OAc)2, PdSO4 and Pd(NO3)2 and best acid HClO4. The solvent is MeCN/water 7:1 w/w, 1-2 % catalyst, best acid conditions 0.15-0.3 M and time is reduced to a bit more than 10 minutes for total conversion of oleofin.
General procedure :
0.2 mmol Pd(AcO)2, benzo 9 mmol, and the inorganic acid, 0.1 M were dissolved in acetonitrile/water 7:1 50 ml. The solution was deoxygenated by purgin with argon for at least 30 min. and stirred vigorously until the Pd(AcO)2 was dissolved. The oleofin 10 mmol was added to the flask by syringe, and the rxn was stirred for 10 min. The products were separated from the catalyst by extraction into hexane or diethyl ether, washed with 30 % NaOH nad analyzed by a capillary GC-internal standard method. It produces as well some other ketones and/or aldehydes like all wackers, and yields more 2 ketone at 23 C or so, with more temp ther's more isomerization and other ketones are produced, yield for 1 decene is 81 %.
JOC 1990, 55, 2924-2927
It would be interesting to test it with our favourite oleofin, but as far I know, nobody have checked it. May be 1 % of catalyst could be used, 0.25 H2SO4 or HClO4, rxn time 2 hours or so to get the ketone.
