Graphene oxide mediated thiolation of indoles in water: a green and sustainable approach to synthesize 3-sulfenylindoles

作者: Min Chen , Yi Luo , Chen Zhang , Li Guo , Qiantao Wang

DOI: 10.1039/C8QO00726H

关键词: Combinatorial chemistrySubstrate (chemistry)OxideGrapheneFunctional groupIodine.freeReagentChemistry

摘要: An atom economical and transition-metal iodine free procedure of graphene oxide (a heterogeneous, recyclable, inexpensive, environment-friendly carbocatalyst) mediated thiolation indoles, using thiols as a thiolating reagent, has been developed. This methodology provides catalyst-recyclable organic-solvent-free protocol to afford 3-sulfenylindoles with good functional group tolerance broad substrate scope.

参考文章(68)
Thomas Hostier, Vincent Ferey, Gino Ricci, Domingo Gomez Pardo, Janine Cossy, TFA-promoted direct C-H sulfenylation at the C2 position of non-protected indoles. Chemical Communications. ,vol. 51, pp. 13898- 13901 ,(2015) , 10.1039/C5CC05421D
Min Chen, Zhi-Tang Huang, Qi-Yu Zheng, Visible light-induced 3-sulfenylation of N-methylindoles with arylsulfonyl chlorides Chemical Communications. ,vol. 48, pp. 11686- 11688 ,(2012) , 10.1039/C2CC36866H
Jaemyung Kim, Laura J. Cote, Franklin Kim, Wa Yuan, Kenneth R. Shull, Jiaxing Huang, Graphene Oxide Sheets at Interfaces Journal of the American Chemical Society. ,vol. 132, pp. 8180- 8186 ,(2010) , 10.1021/JA102777P
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
Paul C. Unangst, David T. Connor, S. Russell Stabler, Robert J. Weikert, Mary E. Carethers, John A. Kennedy, David O. Thueson, James C. Chestnut, Richard L. Adolphson, M. C. Conroy, Novel indolecarboxamidotetrazoles as potential antiallergy agents. Journal of Medicinal Chemistry. ,vol. 32, pp. 1360- 1366 ,(1989) , 10.1021/JM00126A036
Valeria Famiglini, Giuseppe La Regina, Antonio Coluccia, Sveva Pelliccia, Andrea Brancale, Giovanni Maga, Emmanuele Crespan, Roger Badia, Eva Riveira-Muñoz, José A. Esté, Rosella Ferretti, Roberto Cirilli, Claudio Zamperini, Maurizio Botta, Dominique Schols, Vittorio Limongelli, Bruno Agostino, Ettore Novellino, Romano Silvestri, Indolylarylsulfones Carrying a Heterocyclic Tail as Very Potent and Broad Spectrum HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors Journal of Medicinal Chemistry. ,vol. 57, pp. 9945- 9957 ,(2014) , 10.1021/JM5011622
Peng Guo, Huaihe Song, Xiaohong Chen, Hollow graphene oxide spheres self-assembled by W/O emulsion Journal of Materials Chemistry. ,vol. 20, pp. 4867- 4874 ,(2010) , 10.1039/B927302F
Peng Sang, Zhengkai Chen, Jianwei Zou, Yuhong Zhang, K2CO3 promoted direct sulfenylation of indoles: a facile approach towards 3-sulfenylindoles Green Chemistry. ,vol. 15, pp. 2096- 2100 ,(2013) , 10.1039/C3GC40724A
Yunyun Liu, Yi Zhang, Changfeng Hu, Jie-Ping Wan, Chengping Wen, Synthesis of 3-sulfenylated indoles by a simple NaOH promoted sulfenylation reaction RSC Advances. ,vol. 4, pp. 35528- 35530 ,(2014) , 10.1039/C4RA05206D
Sungjin Park, Rodney S. Ruoff, Chemical methods for the production of graphenes. Nature Nanotechnology. ,vol. 4, pp. 217- 224 ,(2009) , 10.1038/NNANO.2009.58