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

Abstract : 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. © 2020 American Chemical Society.
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Submitted on : Thursday, March 5, 2020 - 4:59:11 PM
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J.W. Prybil, R. Wallace, A. Warren, J. Klingman, R. Vaillant, et al.. Silylation of Pyridine, Picolines, and Quinoline with a Zinc Catalyst. ACS Omega, ACS Publications, 2020, 5 (3), pp.1528-1539. ⟨10.1021/acsomega.9b03317⟩. ⟨hal-02500040⟩

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