Applications of phase-transfer catalysis. lxv alkylation of alkynes under phase transfer catalysis
Phenylacetyle ne can be propylated by propyl bromide in toluene at 80-110 °C in the presence of excess powdered potassium hydroxide and 2 mol % of 18-crown-6. Aliphatic alkynes are deprotonated effectively only by NaNH2, NaH, or KH. Whereas this step proceeds without catalyst, subsequent alkylation needs the presence of a PT catalyst at 80 °C in toluene. The most useful catalyst for this conversion is Schwesinger's salt, whase lipophilic cation seems to solubilize the acetylide anion.
Dehmlow, Eckehard Volker,Fastabend, Uwe
p. 53 - 55
(2007/10/03)
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