Organic letters

Synthesis of 2-Aminophenols and Heterocycles by Ru-Catalyzed C–H Mono-and Dihydroxylation

X Yang, G Shan, Y Rao

Index: Yang, Xinglin; Shan, Gang; Rao, Yu Organic Letters, 2013 , vol. 15, # 10 p. 2334 - 2337

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Citation Number: 39

Abstract

A novel and efficient synthesis of 2-aminophenols, 2-aminobenzene-1, 3-diols, and heterocycles through Ru-catalyzed C–H mono-and dihydroxylation of anilides has been developed with a new directing group strategy. The reaction demonstrates excellent reactivity, regioselectivity, good functional group tolerance, and high yields.

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[Ichikawa, Masanori; Yokomizo, Aki; Itoh, Masao; Haginoya, Noriyasu; Sugita, Kazuyuki; Usui, Hiroyuki; Terayama, Koji; Kanda, Akira Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 17 p. 5207 - 5224]

Nucleophilic substitution at nitrogen and carboxyl carbon of N-aryl-O-pivaloylhydroxylamines in aqueous solution: competition with SN1 solvolysis of model …

[Helmick, John S.; Novak, Michael Journal of Organic Chemistry, 1991 , vol. 56, # 8 p. 2925 - 2927]

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[Novak, Michael; Lagerman, Robert K. Journal of Organic Chemistry, 1988 , vol. 53, # 20 p. 4762 - 4769]