Faculty Publications

Title

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

Document Type

Article

Journal/Book/Conference Title

ACS Omega

Volume

5

Issue

3

First Page

1528

Last Page

1539

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.

Original Publication Date

1-28-2020

DOI of published version

10.1021/acsomega.9b03317

Repository

UNI ScholarWorks, Rod Library, University of Northern Iowa

Language

en

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