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Cation Radical Accelerated Nucleophilic Aromatic Substitution via Organic Photoredox Catalysis.

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Nucleophilic aromatic substitution (SNAr) is a direct method for arene functionalization; however, it can be hampered by low reactivity of arene substrates and their availability. Herein we describe a cation… Click to show full abstract

Nucleophilic aromatic substitution (SNAr) is a direct method for arene functionalization; however, it can be hampered by low reactivity of arene substrates and their availability. Herein we describe a cation radical-accelerated nucleophilic aromatic substitution using methoxy- and benzyloxy-groups as nucleofuges. In particular, lignin-derived aromatics containing guaiacol and veratrole motifs were competent substrates for functionalization. We also demonstrate an example of site-selective substitutive oxygenation with trifluoroethanol to afford the desired trifluoromethylaryl ether.

Keywords: radical accelerated; nucleophilic aromatic; accelerated nucleophilic; aromatic substitution; cation radical

Journal Title: Journal of the American Chemical Society
Year Published: 2017

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