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

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 devel...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-03, Vol.89 (6), p.4191-4198
Main Authors: Brodsky, Noah, Phadnis, Nidheesh, Ibrahim, Mohamed, Andino, Isabel M., Giro, Inés Blanc, Milligan, John A.
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c02267