112970-62-4Relevant academic research and scientific papers
Chemoselectivity in the Kosugi-Migita-Stille coupling of bromophenyl triflates and bromo-nitrophenyl triflates with (ethenyl)tributyltin
Ansari, Nurul N.,Cummings, Matthew M.,S?derberg, Bj?rn C.G.
, p. 2547 - 2560 (2018/04/20)
Kosugi-Migita-Stille cross coupling reactions of (ethenyl)tributyltin with all isomeric permutations of bromophenyl triflate and bromo-nitrophenyl triflate were examined in order to determine the chemoselectivity of carbon-bromine versus carbon-triflate bond coupling under different reaction conditions. In general, highly selective carbon-bromine bond cross couplings were observed using for example bis(triphenylphosphine)palladium dichloride (2 mol-%) in 1,4-dioxane at reflux. In contrast, reactions using the same pre-catalyst but in the presence of a three-fold excess of lithium chloride in N,N-dimethylformamide at ambient temperature were in most cases selective for coupling at the carbon-triflate bond. Overall, isolated yields and the selectivity for carbon-bromine bond coupling were significantly higher compared to carbon-triflate bond coupling.
Palladium-Catalyzed Coupling of 2-Bromoanilines with Vinylstannanes. A Regiocontrolled Synthesis of Substituted Indoles
Krolski, Michael E.,Renaldo, Alfred F.,Rudisill, Duane E.,Stille, J. K.
, p. 1170 - 1176 (2007/10/02)
The palladium-catalyzed cross-coupling reaction of aryl halides and triflates with vinylstannane reagents has been used to produce a variety of substituted indoles.The mild reaction conditions and selectivity inherent in the coupling reaction have been utilized to produce regiochemically pure 4-, 5-, and 6-substituted indoles.
