Graphene‐Oxide‐Catalyzed Cross‐Dehydrogenative Coupling of Oxindoles with Arenes and Thiophenols

作者: Hongru Wu , Chuntian Qiu , Zhaofei Zhang , Bing Zhang , Shaolong Zhang

DOI: 10.1002/ADSC.201901224

关键词:

摘要: Here, we explore the GO‐catalyzed cross‐dehydrogenative coupling of oxindoles with arenes and thiophenols for the rapid synthesis of 3‐aryloxindoles and 3‐sulfenylated oxindoles. Control experiments and small‐molecule mimicking studies reveal that the acidic nature and quinone‐type functionalities of GO are synergistically utilized for the coupling reaction. The reaction proceeds under simple and mild reaction conditions, exhibits good functional group tolerance, and can be easily scaled up to the gram level.

参考文章(76)
D. Li, R. B. Kaner, Graphene-based materials Science. ,vol. 320, pp. 1170- 1171 ,(2013) , 10.1126/SCIENCE.1158180
Yarabhally R. Girish, Kothanahally S. Sharath Kumar, Kuntebommanahalli N. Thimmaiah, Kanchugarakoppal S. Rangappa, Sheena Shashikanth, ZrO2-β-cyclodextrin catalyzed synthesis of 2,4,5-trisubstituted imidazoles and 1,2-disubstituted benzimidazoles under solvent free conditions and evaluation of their antibacterial study RSC Advances. ,vol. 5, pp. 75533- 75546 ,(2015) , 10.1039/C5RA13891D
Feng Hu, Mehulkumar Patel, Feixiang Luo, Carol Flach, Richard Mendelsohn, Eric Garfunkel, Huixin He, Michal Szostak, Graphene-Catalyzed Direct Friedel-Crafts Alkylation Reactions: Mechanism, Selectivity, and Synthetic Utility. Journal of the American Chemical Society. ,vol. 137, pp. 14473- 14480 ,(2015) , 10.1021/JACS.5B09636
Cheng-Kang Mai, Matthew F. Sammons, Tarek Sammakia, α-Arylation of 3-Aryloxindoles Organic Letters. ,vol. 12, pp. 2306- 2309 ,(2010) , 10.1021/OL100666V
Chris V. Galliford, Karl A. Scheidt, Natürliche Pyrrolidinylspirooxindole als Vorlagen für die Entwicklung medizinischer Wirkstoffe Angewandte Chemie. ,vol. 119, pp. 8902- 8912 ,(2007) , 10.1002/ANGE.200701342
Feng Zhou, Yun-Lin Liu, Jian Zhou, Catalytic Asymmetric Synthesis of Oxindoles Bearing a Tetrasubstituted Stereocenter at the C‐3 Position Advanced Synthesis & Catalysis. ,vol. 352, pp. 1381- 1407 ,(2010) , 10.1002/ADSC.201000161
Yunfei Cai, Jun Li, Weiliang Chen, Mingsheng Xie, Xiaohua Liu, Lili Lin, Xiaoming Feng, Catalytic Asymmetric Sulfenylation of Unprotected 3-Substituted Oxindoles Organic Letters. ,vol. 14, pp. 2726- 2729 ,(2012) , 10.1021/OL3009446
M. Soledade C. Pedras, Mohammad Hossain, Metabolism of crucifer phytoalexins in Sclerotinia sclerotiorum: detoxification of strongly antifungal compounds involves glucosylation Organic and Biomolecular Chemistry. ,vol. 4, pp. 2581- 2590 ,(2006) , 10.1039/B604400J
Ryan A. Altman, Alan M. Hyde, Xiaohua Huang, Stephen L. Buchwald, Orthogonal Pd- and Cu-Based Catalyst Systems for C- and N-Arylation of Oxindoles Journal of the American Chemical Society. ,vol. 130, pp. 9613- 9620 ,(2008) , 10.1021/JA803179S
Piyasena Hewawasam, Matthew Erway, Sandra L. Moon, Jay Knipe, Harvey Weiner, Christopher G. Boissard, Debra J. Post-Munson, Qi Gao, Stella Huang, Valentin K. Gribkoff, Nicholas A. Meanwell, Synthesis and structure-activity relationships of 3-aryloxindoles: a new class of calcium-dependent, large conductance potassium (maxi-K) channel openers with neuroprotective properties. Journal of Medicinal Chemistry. ,vol. 45, pp. 1487- 1499 ,(2002) , 10.1021/JM0101850