Silylation Of Pyridine, Picolines, And Quinoline With A Zinc Catalyst

Authors

Joshua W. Prybil, University of Northern IowaFollow
Rodney Wallace, University of Northern IowaFollow
Alexandra Warren, University of Northern IowaFollow
Jordan Klingman, University of Northern Iowa
Romane Vaillant, ENSCR Ecole Nationale Supérieure de Chimie de Rennes
Michael B. Hall, Texas A&M UniversityFollow
Xin Yang, Texas A&M UniversityFollow
William W. Brennessel, University of RochesterFollow
Robert M. Chin, University of Northern IowaFollow

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 ahead-to-tail dimerization of N-silyl-1,4-dihydropyridine to form a diazaditwistane molecule.

Department

Department of Chemistry and Biochemistry

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

Recommended Citation

Prybil, Joshua W.; Wallace, Rodney; Warren, Alexandra; Klingman, Jordan; Vaillant, Romane; Hall, Michael B.; Yang, Xin; Brennessel, William W.; and Chin, Robert M., "Silylation Of Pyridine, Picolines, And Quinoline With A Zinc Catalyst" (2020). Faculty Publications. 358.
https://scholarworks.uni.edu/facpub/358