Photochemical proton-coupled C–H activation: an example using aliphatic fluorination
Literature Information
Mackenzie J. Field, Soumalya Sinha
Selective functionalization of unactivated C–H bonds is an ongoing chemical challenge. C–H activation requires the transfer of H+ and e−, so called proton-coupled electron transfer (PCET) reactions. Recent efforts in photochemical PCET involving C–H bonds show great promise for the synthesis of new compounds. One such example is photochemical C–H fluorination reactions. In many cases, the discrete PCET mechanisms are yet to be defined in a systematic way. Here, we investigated electron transfer (ET) and PCET reactions of electronically excited 1,2,4,5-tetracyanobenzene and anthraquinone with the components of typical fluorination reactions. Analysis using kinetic and thermodynamic models, and steady-state and time-resolved fluorescence data, suggest that C–H activation proceeds efficiently where electronically excited sensitizers accept H˙.
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Source Journal
Physical Chemistry Chemical Physics
Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.
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