Citation: Li Hongliang, Wang Zhenglin, Deng Weiping. Cu(I)-Catalyzed Intramolecular Cyclization of Ortho-halogenated Phenylthioacetamides for the Synthesis of 2-Amino Benzo[b]thiophenes[J]. Chinese Journal of Organic Chemistry, ;2016, 36(10): 2419-2425. doi: 10.6023/cjoc201605030 shu

Cu(I)-Catalyzed Intramolecular Cyclization of Ortho-halogenated Phenylthioacetamides for the Synthesis of 2-Amino Benzo[b]thiophenes

1.
Shanghai Key Laboratory of Functional Materials Chemistry & School of Pharmacy, East China University of Science and Technology, Shanghai 200237

Corresponding author: Deng Weiping, weiping_deng@ecust.edu.cn
Received Date: 17 May 2016
Revised Date: 28 June 2016

Fund Project: National Natural Science Foundation of China 21372074

Figures(2)

The Cu(I)-catalyzed intramolecular cyclization of ortho-halogenated phenylthioacetamides to form 2-amino ben-zo[b]thiophenes in water was studied. This method employed water instead of organic solvent, and the catalyst-loading can be as low as to 5 mol% and the yield of products is up to 98%, which overcomes the drawbacks such as harsh reaction conditions and low yields in the previous methods. In addition, the reaction can be scaled up to gram-scale and catalyst can be reused with a maintained yield of products. This reaction provided a simple and environmentally friendly protocol for the preparaion of 2-amino benzo[b]thiophene and their derivatives.
- 2-amino benzo[b]thiophenes,
- Cu-catalyzed,
- water-phase,
- ortho-halogenated phenylthioacetamides
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沈阳化工大学材料科学与工程学院沈阳 110142