Free Standard AU & NZ Shipping For All Book Orders Over $80!
Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
REVIEW

Sulfides Synthesis: Nanocatalysts in C–S Cross-Coupling Reactions

Lotfi Shiri A B , Arash Ghorbani-Choghamarani A B and Mosstafa Kazemi A B
+ Author Affiliations
- Author Affiliations

A Department of Chemistry, Faculty of Basic Sciences, Ilam University, PO Box 69315-516, Ilam, Iran.

B Corresponding authors. Email: lshiri47@gmail.com; arashghch58@yahoo.com; mostafakazemi92@yahoo.com




Lotfi Shiri was born in Baghdad (Iraq). He obtained his B.Sc. in applied chemistry from Mazandaran University and M.Sc. in organic chemistry from Mazandaran University with Professor Mahmood Tajbakhsh in 2001. He received his Ph.D. degree under the supervision of Professor Ramin Ghorbani-Vaghei in 2013. His current interests are the synthesis of N-halo reagents and heterogeneous catalysts and their applications in organic synthesis.



Arash Ghorbani-Choghamarani finished his B.S. studies in applied chemistry at Bu-Ali Sina University, Hamadan, Iran (2001) and received his M.Sc. in organic chemistry under the supervision of Professor Mohammad Ali Zolfigol (2003) and subsequently began his Ph.D. studies in organic chemistry with the same supervisor at the same university. During his Ph.D. program, he completed a sabbatical fellowship with Professor Robert H.E. Hudson at the University of Western Ontario, London, Ontario, Canada (from September 2005 to September 2006). He obtained his Ph.D. degree in 2007. He then joined the Department of Chemistry at Ilam University, Ilam, Iran, as a faculty member. He is currently an associate professor of organic chemistry.



Mosstafa Kazemi was born in Ilam, Iran. He received his M.S. degree in organic chemistry from Ilam University in 2013. Currently, he is working towards his Ph.D. degree under the supervision of Assistant Professor Lotfi Shiri in the Department of Chemistry at Ilam University. His current interests are focussed on the development of new strategies for the synthesis of heterogeneous catalysts, in the form of nanoparticles, and their application in the synthesis organosulfur and heterocyclic compounds in line with the concept of modern green synthetic chemistry.

Australian Journal of Chemistry 69(6) 585-600 https://doi.org/10.1071/CH15528
Submitted: 27 August 2015  Accepted: 9 November 2015   Published: 7 January 2016

Abstract

The C–S cross-coupling reaction of aryl halides with thiols or sulfur sources is a key and valuable synthetic transformation in chemistry and medicine as well as in biology, and the development of novel efficient synthetic protocols for the synthesis of the corresponding products (sulfides) is highly desired. Among a wide range of catalysts used in C–S coupling reactions, metallic nanocatalysts have attracted notable interest. Herein, we summarize recent breakthroughs in the arena of metal nanocatalysts employed in C–S cross-coupling reactions with the goal of stimulating further progress in this field. This review is divided into three main sections according to the nature of the metal nanocatalysts discussed. The first section focuses on naked or purely metallic catalysts in nano-size, such as Cu, Pd, Ni, and In. The second section focuses on the role of Fe3O4 magnetic nanoparticles and mesoporous silica nanomaterials, such as MCM-41 and SBA-15, as catalyst supports. Finally, the third section focuses on the catalytic activities of copper ferrite nanoparticles in C–S cross-coupling reactions. Additionally, the recovery and reusability of the nanocatalyst, which are very important from commercial and economical points of view, are comprehensively discussed in this review.


References

[1]  S. V. Ley, A. W. Thomas, Angew. Chem., Int. Ed. 2003, 42, 5400.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXpsFOqtbk%3D&md5=96a86915ff72bda6f725141ccf5f11cbCAS |

[2]  M. Kazemi, L. Shiri, J. Sulfur Chem. 2015, 36, 613.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXhsVCnsr7P&md5=7018e81a41fb92e28bcc70b0385be273CAS |

[3]  M. Kazemi, L. Shiri, H. Kohzadi, Phosphorus, Sulfur Silicon Relat. Elem. 2015, 190, 1398.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXhtlKltL3J&md5=7b0cb035cf23117f78bd1bd3ca659a06CAS |

[4]  M. Kazemi, L. Shiri, H. Kohzadi, Phosphorus, Sulfur Silicon Relat. Elem. 2015, 190, 978.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXht1aktbvE&md5=b1d30483acd1b33004c14ae07e7b5a0dCAS |

[5]  A. Gangjee, Y. Zeng, T. Talreja, J. Med. Chem. 2007, 50, 3046.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXmtFCnsLo%3D&md5=b7de286c99ef857f18337a59813d4f5fCAS | 17552508PubMed |

[6]  B. S. Giri, R. A. Pandey, Bioresour. Technol. 2013, 142, 420.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhtV2ltrvL&md5=779ce956626119ca17d2bd41f036a08aCAS | 23748090PubMed |

[7]  M. Kazemi, H. Kohzadi, O. Abdi, J. Mater. Environ. Sci 2015, 6, 1451.

[8]  A. E. Czeizel, P. Vargha, Eur. J. Obstet. Gynaecol. 2003, 110, 497.
         | 1:CAS:528:DC%2BD3sXjs1ekt7k%3D&md5=bbe746733875a967f3b6064d83494576CAS |

[9]  I. Cruz, M. E. Cruz, F. Carrasco, J. Horton, J. Neurol. Sci. 1995, 133, 152.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XjvF2itQ%3D%3D&md5=f5a86746de63cea1db8b095fd367adaaCAS | 8583218PubMed |

[10]  C. Mercier-Guyon, J. P. Chabannes, P. Saviuc, Curr. Med. Res. Opin. 2004, 20, 1347.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXhtVSlur7P&md5=874e77d1bc87c335183f05e5061a2fbfCAS | 15383182PubMed |

[11]  S. B. Rho, B. R. Kim, S. Kang, Gynecol. Oncol. 2011, 120, 121.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhsFWqtb%2FE&md5=e172d1d0ae219a814fff2edb92b58f75CAS | 21035837PubMed |

[12]  I. M. Kenawi, B. N. Barsoum, M. A. Youssef, J. Pharm. Biomed. Anal. 2005, 37, 655.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXjt1ajsr4%3D&md5=7969c1393cb1a6036e03799062608921CAS | 15797785PubMed |

[13]  C. M. Tan, G. S. Chen, C. S. Chen, J. W. Chern, J. Chin. Chem. Soc. 2011, 58, 94.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXkvVOgu74%3D&md5=1bd5a45393913c01cca4b9e21adb32fcCAS |

[14]  R. Carlson, Chemom. Intell. Lab. Syst. 2004, 73, 151.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXntlSjtrk%3D&md5=a101cbe03cbf0863fc252ae3fd1d8125CAS |

[15]  S. Reculusa, C. Poncet-Legrend, A. Perro, E. Duguet, E. Bourgeat-Lami, C. Mingotaud, S. Ravaine, Chem. Mater. 2005, 17, 3338.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXksVOku78%3D&md5=528e023f48df72c7bb7f40acd89355abCAS |

[16]  C. B. Murray, D. J. Norris, M. G. Bawendi, J. Am. Chem. Soc. 1993, 115, 8706.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3sXlsV2ltL8%3D&md5=0f8226da560f47ca2952222c01e5f9d0CAS |

[17]  I. Ojima, N. Clos, C. Bastos, Tetrahedron 1989, 45, 6901.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXlsVCntw%3D%3D&md5=4684136bc29843d5917ebf7c311e7e05CAS |

[18]  J. S. Carey, D. Laffan, C. Thomson, M. T. Williams, Org. Biomol. Chem. 2006, 4, 2337.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XlsV2jtr8%3D&md5=b6ad34291951bcdc75198d1ad0d901bfCAS | 16763676PubMed |

[19]  J. W. Jun, J. S. Choi, J. Cheon, Angew. Chem. 2006, 118, 3492.
         | Crossref | GoogleScholarGoogle Scholar |

[20]  R. Narayanan, M. A. El-Sayed, Nano Lett. 2004, 4, 1343.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXktlahsLc%3D&md5=5e097cfc678b8a4f0b2187a4087ddc5cCAS |

[21]  L. Rout, K. S. Tamal, T. Punniyamurthy, Angew. Chem., Int. Ed. 2007, 46, 5583.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXotlCqt7Y%3D&md5=2c00f7e09675618d48eeb13d4e48d1d8CAS |

[22]  B. C. Ranu, A. Saha, R. Jana, Adv. Synth. Catal. 2007, 349, 2690.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhsVyjsLzL&md5=29a18d792a7a4aeaab850b71d7f7dfa2CAS |

[23]  S. Jammi, S. Sakthivel, L. Rout, T. Mukherjee, S. Mandal, R. Mitra, P. Saha, T. Punniyamurthy, J. Org. Chem. 2009, 74, 1971.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXht1OgtbY%3D&md5=c0b324be1c8bc8189d303b7522f3676bCAS | 19173559PubMed |

[24]  V. Prakash-Reddy, K. Swapna, A. Vijay-Kumar, K. Rao, Synlett 2009, 17, 2783.

[25]  K. H. V. Reddy, V. P. Reddy, J. Shankar, B. Madhav, B. S. P. Anil-Kumar, Y. V. D. Nageswar, Tetrahedron Lett. 2011, 52, 2679.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXltFKju7k%3D&md5=525b16357566702d3b49af32b0145042CAS |

[26]  V. K. Akkilagunta, R. R. Kakulapati, J. Org. Chem. 2011, 76, 6819.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXptFKmsrs%3D&md5=9f8b518010a80b0dcb2bb4dbd7283835CAS | 21732640PubMed |

[27]  K. H. V. Reddy, V. P. Reddy, A. A. Kumar, G. Kranthi, Y. V. D. Nageswar, Beilstein J. Org. Chem. 2011, 7, 886.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXosVait7g%3D&md5=dee5df2ea1b64ec943f4643b72066840CAS |

[28]  R. S. Schwab, D. Singh, E. E. Alberto, P. Piquini, O. E. D. Rodrigues, A. L. Braga, Catal. Sci. Technol. 2011, 1, 569.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXnslShs7s%3D&md5=68d5463e0bb900b05878bff40b6e916fCAS |

[29]  H.-J. Xu, Y.-F. Liang, X.-F. Zhoua, Y.-S. Feng, Org. Biomol. Chem. 2012, 10, 2562.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XjsFKltr4%3D&md5=29a09ac6dc423d2c2f475d4a562ba015CAS | 22354412PubMed |

[30]  B. Y. Bhong, A. V. Shelke, N. N. Karade, Tetrahedron Lett. 2013, 54, 739.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhvVyhsr7K&md5=b80a052f16589f07f87343926066a5c2CAS |

[31]  H. Woo, B. Mohan, E. Heo, J. C. Park, H. Song, K. H. Park, Nanoscale Res. Lett. 2013, 390, 1.

[32]  S. Ganesh-Babu, R. Karvembu, Tetrahedron Lett. 2013, 54, 1677.
         | Crossref | GoogleScholarGoogle Scholar |

[33]  X.-M. Wu, G.-B. Yan, Synlett 2015, 26, 537.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXlsFyquw%3D%3D&md5=c7bda9436b283ab45ee29266391ad10fCAS |

[34]  S. S. Zalesskiy, V. P. Ananikov, Organometallics 2012, 31, 2302.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38Xjt1Cis7Y%3D&md5=5177682430ef33a1124ae1392d094105CAS |

[35]  V. P. Ananikov, I. P. Beletskaya, Dalton Trans. 2011, 40, 4011.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXkt1Kgsb4%3D&md5=2c3c33f2890bbfa60ec1cf53a68dcfd3CAS | 21321732PubMed |

[36]  V. P. Reddy, A. V. Kumar, K. Swapna, K. R. Rao, Org. Lett. 2009, 11, 1697.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXjsFemtrw%3D&md5=b8569fca6b627054db4146f6853ab74fCAS | 19301923PubMed |

[37]  A. S. Kashin, V. P. Ananikov, Top. Catal. 2013, 56, 1246.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXpvFShu7k%3D&md5=d8dc58b8e67637e944391178e6c0d041CAS |

[38]  H.-J. Yoon, J-.W. Choi, H. Kang, T. Kang, S.-M. Lee, B.-H. Jun, Y.-S. Lee, Synlett 2010, 16, 2518.

[39]  B. Movassagh, A. Takallou, A. Mobaraki, J. Mol. Catal. A: Chem. 2015, 401, 55.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXjslClsbg%3D&md5=b98f4c6549fd882a21ae2dcdc41485fcCAS |

[40]  C. Gonzalez-Arellano, R. Luque, D. J. Macquarrie, Chem. Commun. 2009, 1410.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXisFKnt70%3D&md5=2dad86306390d56bcf914e305a75df33CAS |

[41]  S. Kovacs, Z. Novak, Org. Biomol. Chem. 2011, 9, 711.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXot1Grtg%3D%3D&md5=81b5226ec0e725e65d265310fa0b85f9CAS | 21079878PubMed |

[42]  R. B. N. Baig, R. S. Varma, Chem. Commun. 2012, 48, 2582.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XitVGgur4%3D&md5=e7b8adbc705d8a7e7d3b61ff11bfd61aCAS |

[43]  Y. Liu, L. Zhou, X. Hui, Z. Dong, H. Zhu, Y. Shao, Y. Li, RSC Adv. 2014, 4, 48980.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhsFOqtLzL&md5=9a02a62a1a623ab843872964d3a51cbfCAS |

[44]  J. Mondal, A. Modak, A. Dutta, A. Bhaumik, Dalton Trans. 2011, 40, 5228.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXlt1Srs7g%3D&md5=3caff2803d2952fa390d59e0debdcc23CAS | 21461432PubMed |

[45]  J. Mondal, A. Modak, A. Dutta, S. Basu, S. Nath-Jha, D. Bhattacharyya, A. Bhaumik, Chem. Commun. 2012, 48, 8000.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhtVegtLfP&md5=54af331d5d4f8730649376e01ca5a4f3CAS |

[46]  M. Cai, R. Yao, L. Chen, H. Zhao, J. Mol. Catal. A: Chem. 2014, 395, 349.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhsVGgt7vO&md5=48731714c04b17437949faf58073f063CAS |

[47]  A. L. Isfahani, I. Mohammadpoor-Baltork, V. Mirkhani, M. Moghadam, A. R. Khosropour, S. Tangestaninejad, M. Nasr-Esfahani, H. A. Rudbari, Synlett 2014, 25, 645.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXptlShsrs%3D&md5=a4ea61dfa0d883d49bc28a43aa115f6eCAS |

[48]  N. R. G. Bandna, A. K. Shil, D. Sharma, P. Das, Tetrahedron Lett. 2012, 53, 5318.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38Xht1WktLbK&md5=c77552ca3df6982d782675c4f9d5a07eCAS |

[49]  A. Kamal, V. Srinivasulu, J. N. S. R. C. Murty, N. Shankaraiah, N. Nagesh, T. C. Reddy, A. V. Subba-Raoa, Adv. Synth. Catal. 2013, 355, 2297.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXht1OitbrF&md5=d928503493dbede7c08446e52496d2caCAS |

[50]  K. Swapna, S. N. Murthy, M. T. Jyothi, Y. V. D. Nageswar, Org. Biomol. Chem. 2011, 9, 5989.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtVWgsrzN&md5=3f1c13b6eae795acd8fd0970a703ec86CAS | 21769376PubMed |

[51]  N. Panda, A. K. Jena, S. Mohapatra, Appl. Catal., A 2012, 433, 258.
         | Crossref | GoogleScholarGoogle Scholar |

[52]  M. Gholinejad, B. Karimi, F. Mansouri, J. Mol. Catal. A: Chem. 2014, 386, 20.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXmtFWjtbs%3D&md5=d55b28d371bb9350b8d83085d3be6dbaCAS |

[53]  A. R. Hajipour, M. Karimzadeh, G. Azizi, Chin. Chem. Lett. 2014, 25, 1382.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhtVanu77E&md5=8b6724b9b19be0906a8b4e53333fd913CAS |