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Citation: Yuanyi Lu, Jun Zhao, Hongshuang Li. Silver-Catalyzed Ring-Opening Minisci Reaction: Developing a Teaching Experiment Suitable for Undergraduates[J]. University Chemistry, ;2024, 39(11): 225-231. doi: 10.3866/PKU.DXHX202401088 shu

Silver-Catalyzed Ring-Opening Minisci Reaction: Developing a Teaching Experiment Suitable for Undergraduates

State Key Laboratory of Advanced Drug Delivery and Release Systems, School of Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250117, China

Received Date: 30 January 2024
Revised Date: 3 April 2024

The substitution of heteroaromatics by nucleophilic carbon-centered radicals is known as the Minisci reaction. In this study, efficient synthesis of 4-(benzo[d]thiazol-2-yl)butan-2-one was achieved through radical alkylation between 1-methylcyclopropan-1-ol and benzo[d]thiazole under silver-catalyzed and aqueous conditions. This method offers advantages such as simple operation procedures, mild reaction conditions, and excellent atom-economy. Undergraduates have successfully validated this reaction, making it a suitable candidate for a teaching experiment that effectively supplements knowledge in radical chemistry.
- Minisci reaction,
- 1-Methylcyclopropan-1-ol,
- Benzo[d]thiazole,
- Radical alkylation,
- Teaching experiment
1. [1]
  Kürti, L.; Czakó, B. Strategic Applications of Named Reactions in Organic Synthesis, 1st ed.; Elsevier Academic Press:Burlington, MA, USA, 2005; pp. 290−291.
2. [2]
  Minisci, F.; Galli, R.; Cecere, M.; Malatesta, V.; Caronna, T. Tetrahedron Lett. 1968, 9 (54), 5609.
3. [3]
  Bacoş, P. D.; Lahdenperä, A. S. K.; Phipps, R. J. Acc. Chem. Res. 2023, 56 (14), 2037.
4. [4]
  Wang, W.; Wang, S. Curr. Org. Chem. 2021, 25 (8), 894.
5. [5]
6. [6]
  Minisci, F.; Vismara, E.; Fontana, F. Heterocycles 1989, 28 (1), 489.
7. [7]
  Minisci, F.; Vismara, E.; Fontana, F.; Morini, G.; Serravalle, M. J. Org. Chem. 1987, 52 (5), 730.
8. [8]
  Lu, S.-C.; Li, H.-S.; Xu, S.; Duan, G.-Y. Org. Biomol. Chem. 2017, 15 (2), 324.
9. [9]
  Babu, K. R.; Zhu, N.; Bao, H. Org. Lett. 2017, 19 (1), 46.
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