Silylation of Pyridine, Picolines, and Quinoline with a Zinc Catalyst. Academic Article uri icon


  • Zn(OTf)2 (OTf- = trifluoromethanesulfonate) catalyzes the silylation of pyridine, 3-picoline, and quinoline to afford the silylated products, where the silyl groups are meta to the nitrogen. The isolated yields of the products range from 41 to 26%. The 2- and 4-picolines yielded the silylmethylpyridines, where the CH3 groups were silylated instead of the ring. The pyridine silylation can occur via two separate pathways, involving either a 1,4- or a 1,2-hydrosilylation of pyridine as the first step. A byproduct of the pyridine silylation is a head-to-tail dimerization of N-silyl-1,4-dihydropyridine to form a diazaditwistane molecule.

published proceedings

  • ACS Omega

author list (cited authors)

  • Prybil, J. W., Wallace, R., Warren, A., Klingman, J., Vaillant, R., Hall, M. B., ... Chin, R. M.

citation count

  • 6

complete list of authors

  • Prybil, Joshua W||Wallace, Rodney||Warren, Alexandra||Klingman, Jordan||Vaillant, Romane||Hall, Michael B||Yang, Xin||Brennessel, William W||Chin, Robert M

publication date

  • January 2020