Abstract
The first example of the sulfinylation of indoles with arylsulfinamides in water in the presence of trifluoroacetic acid as a promoter is described. The reaction occurs smoothly at room temperature under environmentally benign conditions without any catalyst, additive, ligand, or organic solvent. The developed sulfoxide synthetic protocol is attractive due to the use of water as the solvent and provides a novel and efficient route to a wide range of functionalized diaryl sulfoxides.
Similar content being viewed by others
REFERENCES
Fernández, I. and Khiar, N., Chem. Rev., 2003, vol. 103, p. 3651. https://doi.org/10.1021/cr990372u
Bur, S.K. and Padwa, A., Chem. Rev., 2004, vol. 104, p. 2401. https://doi.org/10.1021/cr020090l
Nohara, T., Fujiwara, Y., Komota, Y., Kondo, Y., Saku, T., Yamaguchi, K., Komohara, Y., and Takeya, M., Chem. Pharm. Bull., 2015, vol. 63, p. 117. https://doi.org/10.1248/cpb.c14-00538
Mahale, R.D., Rajput, M.R., Maikap, G.C., and Gurjar, M.K., Org. Process. Res. Dev., 2010, vol. 14, p. 1264. https://doi.org/10.1021/op100075v
Legros, J., Dehli, J.R., and Bolm, C., Adv. Synth. Catal., 2005, vol. 347, p. 19. https://doi.org/10.1002/adsc.200404206
Spencer, C.M. and Faulds, D., Drugs, 2000, vol. 60, p. 321. https://doi.org/10.2165/00003495
Numata, M., Aoyagi, Y., Tsuda, Y., Yarita, T., and Takatsu, A., Anal. Chem., 2007, vol. 79, p. 9211. https://doi.org/10.1021/ac0713860
Yazdanyar, S., Boer, J., Ingvarsson, G., Szepietowski, J.C., and Jemec, G.B.E., Dermatology, 2011, vol. 222, p. 342. https://doi.org/10.1159/000329023
Sheikh, M.C., Iwasawa, T., Nakajima, A., Kitao, A., Tsubaki, N., Miyatake, R., Yoshimura, T., and Morita, H., Synthesis, 2014, vol. 46, p. 42. https://doi.org/10.1055/s-0033-1338550
Han, J., Soloshonok, V.A., Klika, K.D., Drabowicz, J., and Wzorek, A., Chem. Soc. Rev., 2018, vol. 47, p. 1307. https://doi.org/10.1039/c6cs00703a
Lang, X., Hao, W., Leow, W.R., Li, S., Zhao, J., and Chen, X., Chem. Sci., 2015, vol. 6, p. 5000. https://doi.org/10.1039/c5sc01813g
Li, C., Suzuki, K., Mizunoa, N., and Yamaguchi, K., Chem. Commun., 2018, vol. 54, p. 7127. https://doi.org/10.1039/c8cc03519a
Han, Z., Song, J.J., Yee, N.K., Xu, Y., Tang, W., Reeves, J.T., Tan, Z., Wang, X.J., Lu, B., Krishnamurthy, D., and Senanayake, C.H. Org. Process Res. Dev., 2007, vol. 11, p. 605. https://doi.org/10.1021/op700010a
Xue, F., Wang, D., Li, X., and Wan, B., J. Org. Chem., 2012, vol. 77, p. 3071. https://doi.org/10.1021/jo3003562
Yuste, F., Linares, A.H., Mastranzo, V.M., Ortiz, B., Obregón, R.S., Fraile, A., and Ruano, J.L.G., J. Org. Chem., 2011, vol. 76, p. 4635. https://doi.org/10.1021/jo2006335
Miao, T., Li, P., Zhang, Y., and Wang, L., Org. Lett., 2015, vol. 17, p. 832. https://doi.org/10.1021/ol503659t
Kim, D.H., Lee, J., and Lee, A., Org. Lett., 2018, vol. 20, p. 764. https://doi.org/10.1021/acs.orglett.7b03901
Liu, Q., Wang, L., Yue, H., Li, J.S., Luo, Z., and Wei, W., Green Chem., 2019, vol. 21, p. 1609. https://doi.org/10.1039/c9gc00222g
Zhao, W., Yang, C.H., Sun, H.X., Chneg, Z.G., and Chang, T., New J. Chem., 2018, vol. 42, p. 19349. https://doi.org/10.1039/c8nj05170d
Meyer, A.U., Wimmer, A., and König, B., Angew. Chem. Int. Ed., 2017, vol. 56, p. 409. https://doi.org/10.1002/anie.201610210
Li, H.J., Wu, Y.Y., Wu, Q., Wang, R., Dai, C.Y., Shen, Z.L., Xie, C.L., and Wu, Y.C., Org. Biomol. Chem., 2014, vol. 12, p. 3100. https://doi.org/10.1039/c4ob00228h
Li, H.J., Zhao, J.L., Chen, Y.J., Liu, L., Wang, D., and Li, C.J., Green Chem., 2005, vol. 7, p. 61. https://doi.org/10.1039/b417089j
Wang, H.S., Li, H.J., Wang, J.L., and Wu, Y.C., Green Chem., 2017, vol. 19, p. 2140. https://doi.org/10.1039/c7gc00704c
Ji, Y.Z., Li, H.J., Zhang, J.Y., and Wu, Y.C., Eur. J. Org. Chem., 2019, vol. 2019, p. 1846. https://doi.org/10.1002/ejoc.201900097
Ji, Y.Z., Li, H.J., Zhang, J.Y., and Wu, Y.C., Chem. Commun., 2019, vol. 55, p. 11864. https://doi.org/10.1039/c9cc05652a
Ji, Y.Z., Li, H.J.,Yang, H.R., Zhang, Z.Y., Xie, L.J., and Wu, Y.C., Synlett, 2020, vol. 31, p. 349. https://doi.org/10.1055/s-0039-1691563
Ji, Y.Z., Zhang, J.Y., Li, H. J., Han, C.G., Yang, Y.K., and Wu, Y.C., Org. Biomol. Chem., 2019, vol. 17, p. 4789. https://doi.org/10.1039/c9ob00526a
CCDC 2024909 (3b) and CCDC 2024907 (3c) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures
Funding
This research was funded by the National Natural Science Foundation of China (project nos. 21672046 and 21372054), Fundamental Research Funds for the Central Universities (project no. HIT.NSRIF.201708), and Foundation from the Huancui District of the Wehai City.
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
The authors declare no conflict of interest.
Supplementary information
Rights and permissions
About this article
Cite this article
Liu, Y., Zhang, Z.Y., Ji, Y.Z. et al. Efficient Synthesis of 3-(Arenesulfinyl)indoles in Water. Russ J Org Chem 57, 831–841 (2021). https://doi.org/10.1134/S1070428021050109
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428021050109