No abstract

The Suzuki-Miyaura-type cross-coupling reaction of potassium alkyltrifluoroborates with various alkenyl bromides in the presence of 10 mol % of PdCl(2)(dppf)·CH(2)Cl(2) and 3.0 equiv of Cs(2)CO(3) in aqueous toluene at 80 °C provided the desired compounds in 49-95% yields. A variety of functional groups in the potassium alkyltrifluoroborates were tolerated under the basic conditions.

0-Alkyl S-methyl xanthates have been used to convert alcohols to alkyl halides via free-radical pathways. The xanthate esters were readily prepared in high yields and were converted in 8-80% yields to the corresponding alkyl halides by (a) photolysis with 254-nm light in carbon tetrachloride or bromotrichloromethane and (b) by treatment with Cu(I)-Cu(II) halide in acetonitrile. The photochemical transformation gave low yields with highly aliphatic compounds due to carbon tetrachloride-mediated free-radical halogenation reactions. The transformation promoted by Cu(I)-Cu(II) halide competed with an electron-transfer oxidation process. The reaction could not

The synthesis of potassium trifluoro(N-methylheteroaryl)borates and their use in cross-coupling reactions with various aryl and heteroaryl halides to construct N-methyl heteroaryl-substituted aromatic and heteroaromatic compounds are reported.

Potassium imidomethyltrifluoroborate salts were efficiently synthesized. Potassium phthalimidomethyl-trifluoroborate was successfully used in Suzuki–Miyaura-like cross-coupling reactions with a variety of aryl chlorides.