Nickel-Catalyzed Reaction of Arylzinc Reagents with N-Aromatic Heterocycles: A Straightforward Approach to C-H Bond Arylation of Electron-Deficient Heteroaromatic Compounds

摘要

The catalytic direct arylation of aromatic C-H bonds has emerged as an atom-efficient alternative to conventional cross-coupling between halides and organometallics for the synthesis of (hetero)biaryls. Despite significant advancement in this method, C-H bonds in electron-deficient heteroaromatics, such as pyridines and quinolines, are often not directly applicable. This serious limitation of the C-H bond arylation reactions stems from the fact that the vast majority of them depend on either electrophilic substitution or concerted metalation/deprotonation mechanisms, which inherently restricts the substrates to electron-rich or acidic C-H bonds, respectively. We report herein an alternate approach to catalytic C-H bond arylation that is suitable for electron-deficient heteroaromatics.