Photoinduced Halogen Bond Assisted Biaryl Synthesis via 1,4-Aryl Migration

sulfonyl-2-iodobenzamides, which subsequently undergoes a 1,4-aryl migration through a Truce-Smiles-type rearrangement, ultimately affording structurally diverse and valuable functionalized biaryls. Preliminary mechanistic investigations using TEMPO trapping and EPR spectroscopy support the involvement of radical intermediates, while additional studies (UV-vis and NMR) confirm the presence of a halogen-bonding interaction between the amine and the aryl iodide. Moreover, DFT calculations elucidate the preference for ipso substitution over ortho addition and provide insight into the overall reaction pathway.