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An efficient methodology has been developed for the oxidative cross-coupling of vinyl pyridine with various boronic acids catalyzed by palladium. In this reaction, vinyl pyridines reacted with various aryl boronic acids in the presence of 10 mol% palladium(II) trifluoroacetate, 10 mol% 1,10- phenanthroline, and 1 equivalent silver(I) oxide, to give the corresponding aryl vinyl pyridine products as a single stereoisomer, with N,N-dimethylformamide as the solvent and under 1 atmosphere of oxygen gas. The aryl vinyl pyridine products were obtained in moderate to good yields after 24 hours. A mechanism for the reaction is proposed.

The CF2-containing reagent 2 has been conveniently prepared using CF2Br2 as the readily accessible starting material. The fluoride-mediated nucleophilic reactivity of 2 towards aromatic aldehydes has been demonstrated.

The synthesis of cinnamoyl thiourea derivatives from cinnamoyl isothiocyanate (CIT) with substituted aniline (RC6H4NH2) was investigated in the mostly used ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate, [Bmim][BF4]. Significant enhancements in reactivity, yield and reaction rate were achieved. The products could be recovered by simple filtration. [Bmim][BF4] could be recycled simply by removing water under vacuum and reused at least 9 times without significant decrease in activity.