Document Type
Article
Publication Date
2-27-2024
Abstract
Bis(catecholato)silicate salts are easily accessible reagents that can be used to install alkyl fragments through photoredox-enabled cross-coupling. These reagents can incorporate various functional groups including pendant alkyl halides. A halogenated organosilicate reagent was leveraged to develop a one-pot synthesis of tetrahydroquinolines from o-bromosulfonamides, where the bifunctional reagent participates in a nickel/photoredox cross-coupling followed by intramolecular nucleophilic substitution. The functional group tolerance of this cross-coupling strategy allowed for the preparation of a series of substituted tetrahydroquinolines.
Recommended Citation
Brodsky, Noah; Phadnis, Nidheesh; Ibrahim, Mohamed; Andino, Isabel M.; Giro, Inés Blanc; and Milligan, John A., "3-Chloropropylbis(catecholato)silicate as a Bifunctional Reagent for the One-Pot Synthesis of Tetrahydroquinolines from o-Bromosulfonamides" (2024). College of Life Sciences Faculty Papers. Paper 24.
https://jdc.jefferson.edu/jclsfp/24
Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 License.
Language
English
Comments
This article is the author’s final published version in The Journal of Organic Chemistry, Volume 89, Issue 6, 2025, Pages 4191-4198.
The published version is available at https://doi.org/10.1021/acs.joc.3c02267. Copyright © 2024 The Authors. Published by American Chemical Society
Publication made possible in part by support through a transformative agreement between Thomas Jefferson University and the publisher.