Through the use of a Zn(OTf)2 catalyst, a hydrogen atom on pyridine was replaced with a silicon atom to silylate pyridine. Using Et3SiH as the silane, this reaction was carried out at 240 oC for 2 hours to produce 3-(triethylsilyl)pyridine as the main product. Similar reactions were also carried out using the following pyridine derivatives: 2-picoline, 3-picoline, and 4-picoline. The isolated yields ranged from 30 – 42%. The pyridine silylation can occur through either an initial 1,2- or a 1,4-hydrosilylation of pyridine to form a N-silyl-dihydropyridine intermediate. An electrophilic silyl addition to a double bond, followed by a loss of H2 , eventually leads to the silyl group being meta to the nitrogen. The 2- and 4-picoline reactions afforded (silylmethyl)pyridines, with the methyl group being silylated rather than the ring.

Catalytic silylation of pyridine and picolines using Zn(OTf)2

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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