Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 8, Pages 4129-4135Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00036
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Funding
- Natural Science Foundation of China (NSFC) [21402099, 21602116, 21390400]
- Collaborative Innovation Center of Chemical Science and Engineering (Tianjin)
- State Key Laboratory on Elemento-Organic Chemistry
- Fundamental Research Funds for the Central Universities [65141002]
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The recent discovery of the radical reactivity of a few traditionally-electrophilic N-F reagents has sparked a renaissance of radical fluorination. A knowledge of the N-F bond dissociation enthalpies (BDE) of electrophilic N-F reagents is essential for understanding of their reactivities. However, a thorough literature survey revealed that such information is extremely sparse. This prompted us to carry out the first systematic computation on the N-F BDEs of electrophilic N-F reagents. The calculated N-F BDE scale of 88 electrophilic N-F reagents ranges from 49.3 to 80.0 kcal mol(-1) in acetonitrile. The large variety of N-F reagents and wide span of N-F BDEs make the scale a useful tool not only for the future rational design of novel reagents but also for judicious selection of appropriate ones to explore new radical fluorinations.
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