Tailoring the Reactivity of the Langlois Reagent and Styrenes with Cyanoarenes Organophotocatalysts under Visible‐Light
Year: 2021
Type: article
Abstract: The selective one‐step access to fluoroalkylated hexestrol derivatives, nonsteroidal estrogens, is achieved in good to excellent isolated yields under organophotoredox conditions by using the stable and easy to handle Langlois reagent. Furthermore, the challenging selective hydrotrifluoromethylation of styrenes proceeds under mild reaction conditions without the requirement for any additive. We assume that the solvent drives the reaction pathway towards either the reduction or the dimerization of the radical intermediate generated after initial addition of the fluoroalkyl radical to the styrene. The versatility of the developed system is also extended to encompass radical‐radical cross‐coupling as exemplified here using cyanopyridine. Mechanistic investigations including luminescence and EPR spectroscopy allow to shed light on the different mechanisms. magnified image
Source: Advanced Synthesis & Catalysis
Institutions: Lyon 1 Université, Centre National de la Recherche Scientifique, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, Institut National des Sciences Appliquées de Lyon, École d'Ingénieurs en Chimie et Sciences du Numérique, University of Sfax, University of Gafsa, Faculty of Sciences of Sfax, École Normale Supérieure de Lyon, Laboratoire de Chimie, Laboratoire des Multimatériaux et Interfaces
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
Award: G2593899453
OpenAlex ID: W3204479129