What question did this study set out to answer?

The aim is to explore a new method for synthesizing diverse biaryls through 1,4-aryl migration.

May 3, 20261 citations

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

VSVijay Kumar SimhadriIndian Institute of Science Education and Research Thiruvananthapuram ABAkash BisoyiIndian Institute of Science Education and Research Thiruvananthapuram RSRupam SurIndian Institute of Science Education and Research Thiruvananthapuram

Puntos clave

The aim is to explore a new method for synthesizing diverse biaryls through 1,4-aryl migration.
Utilized sulfonyl-2-iodobenzamides to initiate biaryl synthesis.
Conducted mechanistic investigations using TEMPO trapping, EPR spectroscopy, UV-vis, and NMR.
Performed DFT calculations to analyze reaction pathways.
Confirmed the involvement of radical intermediates in the biaryl synthesis.
Validated halogen-bonding interaction between amine and aryl iodide through various spectroscopic methods.
DFT calculations indicated preference for ipso substitution over ortho addition.

Resumen

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.

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