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C(sp3)-F Bond Functionalization of Isoflurane with Complex Phenols for the Synthesis of CF2-Based (Deuterated) Aryl
Sandeep Kumawat1, Kallakuri Leela Manikya Naga Siva Jyothi1, Venkata Narayana Kalevaru2
1Department of Chemistry, Indian Institute of Technology Hyderabad, Kandi, Sangareddy 502 285, Telangana, India.
Abstract:
Defluorination of polyfluorinated aliphatic substances (PFAS) is highly essential due to increasing concerns over PFAS-related environmental issues. In the present study, we demonstrate that commercially available Isoflurane (belongs to PFAS family) can be repurposed as a valuable fluorinated feedstock through selective C(sp3)-F bond functionalization. A simple, transition-metal-free protocol converts Isoflurane into a reactive fluoroalkene intermediate that undergoes nucleophilic addition with complex phenols. This strategy provides access to diverse, valuable CF2-based ethers bearing an additional chloro handle. The method also enables the preparation of deuterated analogues, expanding the toolkit of fluorinated and deuterated motifs for medicinal chemistry.
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