Sequential C–F Bond Functionalizations of Trifluoroacetamides and Acetates via Spin-Center Shifts
Yi-Feng Wang and K. N. Houk describe C–F bond functionalizations via spin-center shifts.
Monofluoro- and difluoro-substituted organic molecules have properties that make them valuable in many applications. New methods to synthesize these molecules attract wide interest. Among various methods reported for accessing fluorinated compounds, introduction of trifluoromethyl groups has been an effective and economical pathway, since many trifluoromethyl sources are inexpensive and readily available. Thus, a large number of defluorination approaches have been developed to produce mono and difluoro compounds. However, selectively producing either difluoro or monofluoro compounds from trifluoro is exceedingly challenging, because when the first C–F bond is broken, the remaining two get weaker, thus often resulting in exhaustive defluorination. According to Professor Yi-Feng Wang from the University of Science and Technology of China (Hefei, P. R. of China) “strategies that selectively snip off one or two C–F bonds would be very valuable in synthetic and medicinal chemistry”. His research program is focused on discovery of new chemical reactivity and synthetic applications of Lewis base–boryl radicals.
For computational studies in this current work Professor Wang’s group collaborated with the group of Professor K. N. Houk from the University of California, Los Angeles, USA.