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 silylmethylpyri...

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Bibliographic Details
Published in:ACS omega 2020-01, Vol.5 (3), p.1528-1539
Main Authors: Prybil, Joshua W, Wallace, Rodney, Warren, Alexandra, Klingman, Jordan, Vaillant, Romane, Hall, Michael B, Yang, Xin, Brennessel, William W, Chin, Robert M
Format: Article
Language:English
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Chemical Sciences
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Summary: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.
ISSN:2470-1343
2470-1343
DOI:10.1021/acsomega.9b03317