Suzuki-Miyaura cross-coupling reaction of monohalopyridines and L-aspartic acid derivative

Suzuki-Miyaura cross-coupling reaction of halogenated pyridines and a borated L-aspartic acid derivative was conducted. The reactivity of chloro-, bromo-, and iodo-pyridines with substituents at the C2, C3, and C4 positions was investigated. Electron density of halogenated pyridines was also estimated by density functional theory (DFT) calculations. The order of experimental yield of halogen substituents was Br > I >> Cl and C3 > C2, C4 whereas the DFT results indicated the reactivity order as I >> Br, Cl and C4 > C2, C3. Optimized experimental conditions (3-bromopyridine) afforded the coupling product quantitatively. (C) 2018 Elsevier Ltd. All rights reserved.