Introduction
While nucleophilic and electrophilic fluorination have made great progress in recent decades [1], the direct fluorination of sp3-carbon centered radical provides a powerful method for the synthesis of alkyl fluorides. In early times, the hazardous, uncontrollable fluorine gas (F2) [2] and hypofluorite (ROF) [3] or costly xenon difluoride (XeF2) [4] were generally employed as the atomic fluorine reagents that restricted the development of this area. Along with the extensive use of stable and easily handling fluorinating agents, such as N-fluorobenzenesulfonimide (NFSI), SelectFluor, and N-fluoropyridinium salts (NFPY), the revival of radical fluorination is aroused [5, 6].
The DFT calculation of N-F bonds in NFSI, SelectFluor, and NFPY was studied by Sammis and coworkers [7]. The BDE (bond dissociation energy) of N-F bond in NFSI (ca. 63 kcal/mol) is similar to that in SelectFluor (ca. 61–62 kcal/mol); the BDE of N-F bond in NFPY (ca. 75–76 kcal/mol) is slightly larger....
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Yan, H., Zhu, C. (2018). NFSI Radical Fluorination for Preparing Alkyl Fluorides. In: Hu, J., Umemoto, T. (eds) Fluorination. Synthetic Organofluorine Chemistry. Springer, Singapore. https://doi.org/10.1007/978-981-10-1855-8_1-1
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DOI: https://doi.org/10.1007/978-981-10-1855-8_1-1
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