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.