American Chemical Society
jo3c02267_si_001.pdf (20.12 MB)

3‑Chloropropylbis(catecholato)silicate as a Bifunctional Reagent for the One-Pot Synthesis of Tetrahydroquinolines from o‑Bromosulfonamides

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journal contribution
posted on 2024-02-27, 22:04 authored by Noah Brodsky, Nidheesh Phadnis, Mohamed Ibrahim, Isabel M. Andino, Inés Blanc Giro, John A. Milligan
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.