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Ring-Opening Fluorination of Bicyclic Azaarenes
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We have discovered a ring-opening fluorination of bicyclic azaarenes. Upon treatment of bicyclic azaarenes such as pyrazolopyridines with electrophilic fluorinating agents, fluorination of the aromatic ring is followed by a ring-opening reaction. Although this overall trans-formation can be classified as an electrophilic fluorination of an aromatic ring, it is a novel type of fluorination that results in construction of tertiary carbon–fluorine bonds. The present protocol can be applied to a range of bicyclic azaarenes, tolerating azines and a variety of functional groups. Additionally, mechanistic studies and enantioselective fluorination have been examined.
American Chemical Society (ACS)
Title: Ring-Opening Fluorination of Bicyclic Azaarenes
Description:
We have discovered a ring-opening fluorination of bicyclic azaarenes.
Upon treatment of bicyclic azaarenes such as pyrazolopyridines with electrophilic fluorinating agents, fluorination of the aromatic ring is followed by a ring-opening reaction.
Although this overall trans-formation can be classified as an electrophilic fluorination of an aromatic ring, it is a novel type of fluorination that results in construction of tertiary carbon–fluorine bonds.
The present protocol can be applied to a range of bicyclic azaarenes, tolerating azines and a variety of functional groups.
Additionally, mechanistic studies and enantioselective fluorination have been examined.
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