Very interesting article, to my mind its future:
Palladium-Catalyzed Mono-?-arylation of Acetone with Aryl Halides and Tosylates
« on: October 22, 2011, 03:27:41 PM »














1-Chloro-3-phenylprop-2-ene.5s Concentrated aqueous HCI (50 mL)
was added over 1 min to a stirred solution of cinnamyl alcohol (21 g) in
T H F (50 mL), whereafter the solution became heterogeneous. The
mixture was vigorously stirred for 15 min and was then poured into water
and was extracted with CH2CI,. The CH2CI2 was washed twice with
water, once with aqueous NaHCO,, with water again, and dried (MgS-
04). On removal of the solvent, a yellow oil remained which was distilled
a t 45 mm (bp 105 "C) through a 15-cm vacuum-jacketed Vigreux col-
umn to give 20.4 g of pure cinnamyl chlorid
Hz, 1 H) , 1.38 (s, 3 H ) , 1.32 (d, J = 7 Hz, 3 H) , 1.20 (s, 3 H) .
Palladium chloride (1.77 g) and lithium
chloride (1.77 g) were dissolved in hot water (2.5 mL) and then cinnamyl
chloride (6.2 g) in ethanol (20 mL) was added. Carbon monoxide was
bubbled through the solution a t 25 OC and after 15 min orange crystals
began to form and after a total of 3 h, the carbon monoxide flow was
discontinued and the mixture was stirred under carbon monoxide for 20
h a t 25 OC and for a further 24 h a t 0 OC. The product was then filtered
and was washed with methanol followed by ether. The orange powder
was recrystallized from chloroform by the addition ether (2.3 g, 90%).




