Copper-Mediated Direct Alkoxylation of Arenes Using an N,O-Bidentate Directing System
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- 作者：Lin-Bao Zhang ; Xin-Qi Hao ; Shou-Kun Zhang ; Ke Liu ; Baozeng Ren ; Jun-Fang Gong ; Jun-Long Niu ; Mao-Ping Song
- 刊名：Journal of Organic Chemistry
- 出版年：2014
- 出版时间：November 7, 2014
- 年：2014
- 卷：79
- 期：21
- 页码：10399-10409
- 全文大小：616K
- ISSN：1520-6904
文摘
Highly effective CuCl-mediated C鈥擧 alkoxylation of arenes and heteroarenes has been developed by using a 2-aminopyridine 1-oxide moiety as an N,O-bidentate directing group. The reaction proceeds smoothly using a broad range of substrates to afford o-alkoxylated benzoic and heteroaromatic amide products. Moreover, the reaction system shows remarkable compatibility when hexafluoroisopropanol is used as a coupling parter; halogen, nitro, ether, alkoxy, ester, and sulfonyl functional groups are all tolerated. The directing group can be easily removed by base hydrolysis, affording o-alkoxylated benzoic acids.