Nitrogen-to-functionalized carbon atom transmutation of pyridine. Academic Article uri icon

abstract

  • The targeted and selective replacement of a single atom in an aromatic system represents a powerful strategy for the rapid interconversion of molecular scaffolds. Herein, we report a pyridine-to-benzene transformation via nitrogen-to-carbon skeletal editing. This approach proceeds via a sequence of pyridine ring-opening, imine hydrolysis, olefination, electrocyclization, and aromatization to achieve the desired transmutation. The most notable features of this transformation are the ability to directly install a wide variety of versatile functional groups in the benzene scaffolding, including ester, ketone, amide, nitrile, and phosphate ester fragments, as well as the inclusion of meta-substituted pyridines which have thus far been elusive for related strategies.

published proceedings

  • Chem Sci

author list (cited authors)

  • Wu, F., Lenz, M., Suresh, A., Gogoi, A. R., Tyler, J. L., Daniliuc, C. G., Gutierrez, O., & Glorius, F.

complete list of authors

  • Wu, Fu-Peng||Lenz, Madina||Suresh, Adhya||Gogoi, Achyut R||Tyler, Jasper L||Daniliuc, Constantin G||Gutierrez, Osvaldo||Glorius, Frank