Nucleophilic aromatic substitution (SNAr) is a classic reaction with well-known reactivity patterns using electron-poor fluoroarenes. However, the use of electron-neutral and electron-rich substrates is underrepresented in the literature. This presentation will discuss our approach to achieve polarity-reversed SNAr of fluoroarenes. Visible light organic photoredox catalysis enables the functionalization of both electron-neutral and electron-rich fluoroarenes with a broad array of nucleophiles, including azoles, primary amines, and carboxylic acids. The site selectivity of the transformation is dictated by arene electronics. This study establishes an entire new class of fluoroarenes as suitable SNAr substrates which were previously limited or unamenable toward such reactivity.

Nucleophilic aromatic substitution of unactivated fluoroarenes using organic photoredox catalysis

ACS Fall 2021

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