American Chemical Society
ja7b10076_si_001.pdf (11.12 MB)

Cation Radical Accelerated Nucleophilic Aromatic Substitution via Organic Photoredox Catalysis

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journal contribution
posted on 2017-10-25, 00:00 authored by Nicholas E. S. Tay, David A. Nicewicz
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.