meta -Selective Arylation of Pyridine N -Oxides Enabled by ortho -Diiodobenzene Derivatives as Aryne Precursors

A new method for the meta-arylation of pyridine N-oxides that employs o-diiodobenzene derivatives as convenient aryne precursors is reported. In contrast to the Kobayashi precursors, o-diiodobenzenes are either commercially available or readily prepared from simple starting materials and generate arynes under mild conditions via NaH-mediated activation. Our approach not only significantly expands the substrate scope of pyridine N-oxides but also offers an operationally simpler and complementary route to 3-arylpyridines.