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Cation Radical Accelerated Nucleophilic Aromatic Substitution via Organic Photoredox Catalysis

Author:
Tay, Nicholas E. S., Nicewicz, David A.
Source:
Journal of the American Chemical Society 2017 v.139 no.45 pp. 16100-16104
ISSN:
1520-5126
Subject:
Lewis bases, aromatic hydrocarbons, catalytic activity, cations, guaiacol, redox reactions
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.
Agid:
5860392