Late‐Stage Functionalization Using a Popular Titrating Agent: Aryl‐Chlorides and ‐Fluorides Activation by the Diphenylacetic Acid Dianion
Year: 2024
Type: article
Abstract: Aryl-chlorides and -fluorides are common building blocks, but their use in synthesis is limited by the high stability of their Ar-X bonds. The generation of aryl radicals via activation of strong Ar-X bonds is possible through the irradiation of tailor-made organic anions, which become reductants stronger than lithium metal. We report that the combination of visible light with the cheap diphenylacetic acid dianion is an even better tool, showing excellent activity across a variety of complex substrates and providing opportunities for late-stage drug modification. Ar-X bonds are chemoselectively activated in the presence of more easily reducible functions, such as Alk-Cl ones and carbonyl groups. These results pave the way to original synthetic strategies that would be otherwise considered impossible.
Source: Chemistry - A European Journal
Authors: Alessandro Cerveri, Giulia Russo, Sara Sparascio, Daniele Merli, Raimondo Maggi, Nicola Della Ca', Matteo Lanzi, Giovanni Maestri
Institutions: University of Parma, University of Pavia
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,640
Awards: G4421780244, G8474955146
OpenAlex ID: W4403805672