ol802024j_si_001.pdf (1.31 MB)
First Cross-Coupling Reaction of Potassium Aryltrifluoroborates with Organic Chlorides in Aqueous Media Catalyzed by an Oxime-Derived Palladacycle
journal contributionposted on 2008-11-06, 00:00 authored by Emilio Alacid, Carmen Nájera
Potassium aryltrifluoroborates are cross-coupled with aryl and heteroaryl chlorides using a 4-hydroxyacetophenone oxime-derived palladacycle as precatalyst, K2CO3 as base, and TBAB as additive in refluxing water under conventional and microwave heating affording the corresponding biphenyls under phosphine-free conditions. For the arylation of allyl and benzyl chlorides, KOH is used as base in acetone−water (3:2) at rt or 50 °C using 0.1 mol % Pd loading providing allylbenzenes and diarylmethanes, respectively.
KOHbiphenylacetone0.1Organic Chloridesbenzyl chloridesPdpalladacyclerefluxing waterhydroxyacetophenonertloadingadditivearyltrifluoroborateallylprecatalystheteroaryl chloridesK 2COdiarylmethanePotassium AryltrifluoroboratesarylationmolAqueous Media CatalyzedFirstTBABmicrowave heatingPalladacycleallylbenzene