Silylation of Pyridine, Picolines, and Quinoline with a Zinc Catalyst

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.