Document Type : Review Article
Authors
1 Department of Chemistry, Payame Noor University, Tehran, P.O. Box 19395-4697, Iran
2 Faculty of Chemical Sciences, Complutense University of Madrid, Spain
3 Department of Chemistry, Faculty of Basic Sciences, Ilam University, P.O. Box 69315-516, Ilam, Iran
Abstract
The hazardous and toxic nature of many solvents, in particular organic solvents that are extensively used in large scale for organic reactions have transformed a serious threat to the environment. Therefore, the design of solvent-free catalytic reaction has received considerable attention during recent times in the field of green synthesis. A solvent-free or solid state reaction may be accomplished using the reactants single or merge them in clays, zeolites, silica, alumina or other substrates. Esters, thioesters and amides are important and valuable compounds in the area of industry, medicine, pharmaceutical and heterocyclic chemistry. In this paper, various solvent-free systems to synthesize esters, thioesters and amides via the acylation of alcohols, phenols, thiols and amines are described. In this review we summarized the activities presented mainly the recent years.
Graphical Abstract
)
Keywords
Main Subjects
2. N.V. Plechkova, K.R. Seddon, Chem. Soc. Rev. 2008, 37, 123.
3. Y. Zhang, B.R. Bakshi, E.S. Demessie, Environ. Sci. Technol. 2008, 42, 1724.
4. M. Poliakoff, P. Licence, Green chem. 2007, 450, 810.
5. Y. Gu, J.F. Erome, Green Chem. 2010, 12, 1127.
6. T.W. Greene, P.G.M. Wuts, Protective Groups in Organic Synthesis, 3 nd Edition, John Wiley and Son Inc, NewYork, 1999, 150.
7. X.L. Sun, T. Kai, H. Takayanagi, K. Furuhata, Synlett. 1999, 9, 1399.
8. J.S. Yadav, A.V. Narsaiah, A.K. Basak, G.P. Roud, D. Sreenu, K. Nagaiah, J. Mol. Catal. A Chem. 2006, 255, 78.
10. F.R. Van-Heerden, J.J. Huyser, D. Bradley, G. Williams, C.W. Holzapfel, Tetrahedron Lett. 1998, 39, 5281.
11. M. Sandberg, L.K. Sydnes, Tetrahedron Lett. 1998, 39, 6361.
12. B.M. Trost, C.B. Lee, J. Am. Chem. Soc. 2001, 123, 3687.
13. A.P Abbott, T.J. Bell, S. Handa, B. Stoddart, Green Chem. 2005, 705.
14. M. Adinolfi, G. Barone, A. Iadonisi, M. Schiattarella, Tetrahedron Lett. 2003, 44, 4661.
15. J. Iqbal, R.J. Srivastava, Org. Chem. 1992, 57, 2001.
16. S. Ahmed, J. Iqbal, Tetrahedron Lett. 1996, 27, 3791.
17. P. Saravanan, V.K. Singh, Tetrahedron Lett. 1999, 40, 2611.
18. K.L. Chandra, P. Saravanan, R.K. Singh, V.K. Singh, Tetrahedron. 2002, 58, 1369.
19. A. Temperini, D. Annesi, T. Lorenzo, M. Tiecco, Tetrahedron Lett. 2010, 51, 5368.
20. S.K. De, Tetrahedron Lett. 2004, 45, 2919.
21. A. Orita, C. Tanahashi, A. Kakuda, J. Otera, Angew Chem Int Ed. 2000, 39, 2877.
22. A. Orita, C. Tanahashi, A. Kakuda, J. Otera, J. Org. Chem. 2001, 66, 8926.
23. G. Cravotto, P. Cintas, Chem. Soc. Rev. 2006, 35, 180.
24. A. Duarte, W. Cunico, C.M.P. Pereira, A.F.C. Flores, R.A. Freitag, Ultrasonics Sonochem. 2010, 17, 281.
25. S.A. Forsyth, D.R. Mac-Farlane, R.J. Thompson, M.V. Itzstein, Chem Commun. 2002, 714.
26. S.T.A. Shah, K.M. Khan, H. Hussain, M.U. Anwar, M. Fecker, Tetrahedron. 2005, 61, 6652.
27. S.T.A. Shah, K.M. Khan, A.M. Heinrich, W. Voelter, Tetrahedron Lett. 2002, 43, 8281.
28. B. Karimi, H. Seradj, Synlett. 2001, 519.
29. N. Narender, P. Srinivasu, S.J. Kulkarni, K.V. Raghavan, Synth Commun. 2000, 30, 1887.
30. P. Kumar, R.K. Pandey, M.S. Bodas, M.K. Dongare, Synlett. 2001, 206.
31. W. Dan, H. Deng, J. Chen, M. Liu, J. Ding, H. Wu, Tetrahedron. 2010, 66, 7384.
32. M. Hatano, Y. Furuya, T. Shimmura, K. Moriyama, S. Kamiya, T. Maki, K. Ishihara, Org. Lett. 2011, 13, 426.
33. N. Iranpoor, H. Firouzabadi, E. Etemadi-Davan, Tetrahedron Lett. 2013, 54, 1813.
34. M. Kazemi, M. Soleiman-Beigi, Organic Chem Curr Res. 2013, 2, 1.
35. M. Kazemi, H. Kohzadi, Z. Noori, Iran Chem Commun. 2014, 2, 39.
36. Y. J. Marcus, Chem. Soc. 1994, 2, 1751.
37. J.I. Garcia, H. Garcia-Marın, J.A. Mayoral, P. Erez, Green Chem. 2010, 12, 426.
38. R. Gani, C. Jimenez-Gonzalez, D.J.C. Constable, Comput. Chem. Eng. 2005, 29, 1661.
39. R.K. Henderson, C. Jimenez-Gonzalez, D.J.C. Constable, Green. Chem. 2011, 13, 854.
40. Y.W. Dong, G.W. Wang, L. Wang. Tetrahedron. 2008, 64, 10148.
41. H.M. Marvaniya, K.N. Modi, D.J. Sen, Int. J. Drug Dev. Res. 2011, 3, 42.
42. G. Nagendrappa, Resonance. 2002, 7, 59.
43. G. Nagendrappa, Resonance. 2002, 7, 64.
44. A. Baron, J. Martinez, F. Lamaty, Tetrahedron Lett. 2010, 51, 6246.
45. J.G. Hernandez, E. Juaristi, J. Org. Chem. 2011, 76, 1464.
46. G. Guillena, M.d.C. Hita, C.Najera, S.F. Viozquez, Tetrahedron: Asymmetry. 2007, 18, 2300.
47. M.P. Bhaskar, D. Loganthan, Ind. J. Chem. 2004, 43, 892.
48. A.T. Khan, H.L. Choudhury, S. Ghosh, Eur. J. Org. Chem. 2005, 2782.
49. R. Ghosh, S. Maiti, A. Chakraborty, Tetrahedron Lett. 2005, 46, 147.
50. M. Hosseini-Sarvari, H. Sharghi, Tetrahedron. 2005, 61, 10903.
51. F.M. Moghaddam, H. Saeidian, Mate. Sci. Engin. 2007, 139, 265.
52. F. Tammaddon, M.A. Amrollahi, L. Sharafat, Tetrahedron Lette. 2005, 46, 7841.
53. B.P. Bandgar P.E. More, V.T. Kamble, S.S. Sawant, Australian J. Chem. 2009, 61, 1006.
54. A.T. Khan, S. Islam, A. Majee, T. Chattopadhyay, S. Ghosha, J. Mol. Catal. A Chem. 2005, 239, 158.
55. K. Jeyakumar, D.K. Chand, J. Mol. Catal. A Chem, 2006, 255, 275.
56. K. Jeeva Ratnama, R. Sudarshan Reddy, N.S. Sekhar, M. Lakshmi Kantama, F. Figueras, J. Mol. Catal. A Chem. 2007, 276, 230.
57. A. Sakakura, K. Kawajiri, T. Ohkubo, Y. Kosugi, K. Ishihara, J. Am. Chem. Soc. 2007, 129, 14775.
58. L. Zhang, Y. Luo, R. Fan, J. Wu, Green Chem. 2007, 9, 1022.
59. S. Rajesh Gulhane, K. Asit, J. Mol. Catal. A Chem. 2007, 264, 208.
60. S.T. Kadam, S.S. Kim, Synthesis. 2008, 267.
61. G. Meshram, V.D. Patil, Synth. Commun. 2009, 24, 4384.
62. G. Meshram, V.D. Patil, Synth. Commun. 2009, 14, 2516.
63. A.K. Chakraborti, R. Gulhane, Tetrahedron Lett. 2003, 44, 6749.
64. S. Farhadi, M. Zaidi, J. Mol. Catal. A Chem. 2009, 299, 18.
65. R. Qiu, Y. Zhu, X. Xu, Y. Li, L. Shao, X. Ren, X. Cai, D.
An, Y, Shuangfeng. Catal. Commun. 2009, 10, 1889.
66. S.T. Kadam, H. Lee, S.S. Kim, Bull. Korean Chem. Soc. 2009, 30, 1071.
67. M.A. Pasha, M.B. Madhusudana Reddy, K. Manjula, Eur. J. Chem. 2010, 1,1385.
68. R. Qiu, G. Zhang, X. Ren, X. Xu, R. Yang, S. Luo, S. Yin, J. Organomet. Chem. 2010, 695, 1182.
69. R. Das, D. Chakraborty, Synthesis. 2011, 10, 1621.
70. A.R. Shafeek, M. Suleman, Y. Inamdar Mohsinkhan, S. Pathan Santosh, Open Journal of Synthesis Theory and Applications. 2012, 1, 31.
71. A. Mirzaie, J. Med. Chem. Sci. 2019, 1, 5.
72. K. Swapna, S.N. Murthy, Y.V.D. Nageswar, Eur. J. Org. Chem. 2011, 1940.
73. M. Gholinejad, B. Karimi, F. Mansouri, J. Mol. Catal. A Chem. 2014, 386, 20.
74. A. Sajjadi, S.M. Moosavi, J. Med. Chem. Sci. 2019, 1, 9.
75. F. Matloubi Moghaddama, M. Doulabi, H. Saeidian, Scientia Iranica. 2012, 19, 1597.
76. G.Li, G. Zhao, Synth. Commun., 2012, 43, 34-43.
77. R. K. Sodhi, V.Kumar, S. Paul, Open Catal. J. 2013, 6, 1.
78. M.M. Mojtahedi, S. Samadian, J. Chem. 2013, 1.
79. M. Esmaeilpour, A.R. Sardarian, Iranian. J. Sci. Technol. 2014, 38, 175.
80. S.K. Prajapti, A. Nagarsenkar, B. Nagendra Babu, Tetrahedron Lett. 2014, 55, 1784.
81. N. Ghaffari Khaligh, P. Ghods Ghasem‐Abadi, Chin. J. Catal. 2014, 35, 1126.
82. Z. Chemat-Djenni, B. Hamada, F. Chemat, Molecules. 2007, 12, 1399.
83. A. Kappe, Angew. Chem. 2013, 52, 1088.
84. B.P. Bandgar, S.P. Kasture, V.T. Kamble, 2001, 31, 2255.
85. U.V.Mallavadhani, L. Sahoo, S. Roy, Indian. J .Chem. 2004, 43, 2175.
86. V. Constantinou-Kokotou, A. Peristeraki, Synth. Commun. 2004, 22, 4227.
87. K.V.V. Krishna Mohan, N. Narender, S. Kulkarni, J.Green Chem. 2006, 8, 368.
88. J. Li, L. Zhang, F. Peng, J. Bian, T. Yuan, F. Xu, R. Sun, Molecules. 2009, 14, 3551.-3566.
89. M. Mazaheritehrani, J.R. Asghari, L. Orimi, S. Pahlavan, Asian J. Chem. 2010, 22, 2554.
)