Abstract
A simple, one-pot, efficient and novel protocol has been developed for direct synthesis of symmetrical organic disulfides by domino reaction of aryl halides and K2S in the presence of magnetic Fe3O4 nanoparticles as a readily available, highly efficient and recyclable catalyst. A variety of diaryl disulfides can be obtained in good-to-excellent yields up to 98%.
Similar content being viewed by others
References
R.A. Sheldon, H.V. Bekkum, Fine Chemicals Through Heterogeneous Catalysis (Wiley, Weinheim, 2001)
T. Cheng, D. Zhang, H. Li, G. Liu, Green Chem. 16, 3401 (2014)
Y.W. Jun, J.S. Choi, J. Cheon, Angew. Chem. Int. Ed. 45, 3414 (2006)
N.O. Nunez, P. Tartaj, P. Morales, R. Pozas, M. Ocana et al., Chem. Mater. 15, 3558 (2003)
V. Polshettiwar, R. Luque, A. Fihri et al., Chem. Rev. 111, 3036 (2011)
V.R. Calderone, N.R. Shiju, D. Curulla-Ferré et al., Angew. Chem. Int. Ed. 52, 4397 (2013)
M. Zarghani, B. Akhlaghinia, RSC Adv. 6, 38592 (2016)
A. Jutand, S. Negri, A. Principaud, Eur. J. Org. Chem. 2005, 631 (2005)
R.J. Cremlyn, An Introduction to Organosulfur Chemistry (Wiley, New York, 1996)
T.M. Postma, F. Albericio, Eur. J. Org. Chem. 2014, 3519 (2014)
A.P. Umali, E.E. Simanek, Org. Lett. 5, 1245 (2003)
C. Naumann, S. Place, J.C. Sherman, J. Am. Chem. Soc. 124, 16 (2002)
Y. Furusho, T. Oku, T. Hasegawa, A. Tsuboi, N. Kihara, T. Takata, Chem. Eur. J. 9, 2895 (2003)
K.R. West, K.D. Bake, S. Otto, Org. Lett. 7, 2615 (2005)
S.W. Tam-Chang, J.S. Stehouwer, J. Hao, J. Org. Chem. 64, 334 (1999)
T. Tankam, K. Poochampa, T. Vilaivan, M. Sukwattanasinitt, S. Wacharasindhu, Tetrahedron 72, 788 (2016)
B. Mandal, B. Basu, RSC Adv. 4, 13854 (2014)
L. Khanna, P. Khanna, C.S. Panda, S. Panda, Mini Rev. Org. Chem. 10, 268 (2013)
J. Leng, S.-M. Wang, H.-L. Qin, Beilstein J. Org. Chem. 13, 903 (2017)
J.T. Reeves, K. Camara, Z.S. Han, Y. Xu, H. Lee, C.A. Busacca, C.H. Senanayake, Org. Lett. 16, 1196 (2014)
C.B. Kelly, C. Lee, N.E. Leadbeater, Tetrahedron Lett. 52, 4587 (2013)
M. Soleiman-Beigi, M. Alikarami, F. Mohammadi, A. Izadi, Lett. Org. Chem. 10, 622 (2013)
M. Soleiman-Beigi, A. Izadi, J. Chem. 2013, 1–5 (2013)
M. Soleiman-Beigi, F. Mohammadi, Tetrahedron Lett. 53, 7028 (2012)
M. Soleiman-Beigi, M. Hemmati, Appl. Organomet. Chem. 27, 734 (2013)
M. Soleiman-Beigi, Z. Arzehgar, J. Sulfur Chem. 36, 395 (2015)
M. Soleiman-Beigi, F. Mohammadi, Synlett 26, 911 (2015)
M. Soleiman-Beigi, F. Mohammadi, Catal. Lett. 146, 1497 (2016)
S. Laurent, D. Forge, M. Port, A. Roch, C. Robic, L. Vander Elst, R.N. Muller, Chem. Rev. 108, 2064 (2008)
P. Ghosh, B. Saha, G.C. Pariyar, A. Tamang, R. Subba, Tetrahedron Lett. 57, 3618 (2016)
S. Peng, S. Sun, Angew. Chem. 119, 4233 (2007)
M. Soleiman-Beigi, Z. Arzehgar, Monatshefte Chem. Chem. Mon. 147, 1759 (2016)
W.Y. Wu, J.C. Wang, F.Y. Tsai, Green Chem. 11, 326 (2009)
Acknowledgements
We acknowledge the financial support of Ilam University Research Council.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Soleiman-Beigi, M., Mohammadi, K. & Mohammadi, F. Magnetic iron oxide nanoparticles/K2S: a simple and scale-up method for the direct synthesis of symmetrical disulfides from aryl halides. J IRAN CHEM SOC 15, 1545–1550 (2018). https://doi.org/10.1007/s13738-018-1352-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s13738-018-1352-9