Cation Radical Accelerated Nucleophilic Aromatic Substitution via Organic Photoredox Catalysis

被引：177

作者：

Tay, Nicholas E. S. ^{[1
]}

Nicewicz, David A. ^{[1
]}

机构：

[1] Univ North Carolina Chapel Hill, Dept Chem, Chapel Hill, NC 27599 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2017年 / 139卷 / 45期

基金：

美国国家卫生研究院;

关键词：

ARYL; CLEAVAGE; ETHERS;

D O I：

10.1021/jacs.7b10076

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：16100 / 16104

页数：5

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