Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 45, Pages 16100-16104Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b10076
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Funding
- National Institutes of Health [NIGMS R01 GM120186]
- David and Lucile Packard Foundation
- NSF Graduate Fellowship
- U.S. Department of Energy, Office of Basic Energy Sciences [DE-SC0001011]
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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 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.
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