Ring-opening fluorination of bicyclic azaarenes
Masaaki Komatsuda, Ayane Suto, Hiroki Kondo, Hiroyuki Takada, Kenta Kato, Bunnai Saito, Junichiro Yamaguchi
Abstract
]pyridines with electrophilic fluorinating agents, fluorination of the aromatic ring is followed by a ring-opening reaction. Although this overall transformation 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.
Topics & Concepts
Bicyclic moleculeRing (chemistry)ElectrophileChemistryElectrophilic fluorinationMedicinal chemistryOrganic chemistryCombinatorial chemistryStereochemistryCatalysisFluorine in Organic ChemistrySynthesis and Reactions of Organic CompoundsInorganic Fluorides and Related Compounds