Heteroaromatic molecules represent a wide class of natural products and drugs.  Radical derivatizations of these molecules allows access to new frameworks.  Radical reactivity, like two-electron reactivity, depends on the polarity of the reactive site.  Nucleophilic radicals react preferentially with electrophilic radicals and/or substrates, and vice versa.  This selectivity has been utilized extensively to directly couple substrates of opposite polarity.  Methods that reverse the polarity of an active radical in a system have been developed to induce new bond forming reactions.  However, the utilization of radical polarity reversal to functionalize heteroarenes is limited.  In an effort to expand the utility of this process, a polarity-reversed radical cascade has been developed, where an electrophilic radical is generated and selectively reacted with one substrate to form a nucleophilic radical that can then undergo addition into the desired heteroarene.  This polarity-reversed radical cascade allows two selective bond forming events to occur, with complete regioselectivity, for the construction of functionalized heteroarenes.<br/>

Polarity-reversed radical cascade for the functionalization of heteroarenes

253rd National Meeting (2017)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.