Abstract
An environmentally benign and highly efficient procedure for the C–C cross-coupling reactions of aryl halides with olefinic compounds has been developed under ultrasonic irradiation in water in the presence of PEDOT nanofibers/Pd(0) composites (PEDOT-NFs@Pd) as a new recyclable catalyst. PEDOT-NFs@Pd catalyzed the reaction efficiently without using any other harmful organic ligands. Cleaner reaction profile, easy workup procedure, high yields and short reaction time duration are some remarkable features of this method. The utilization of ultrasound irradiation offers a fast, clean and versatile synthetic tool that is often unavailable by conventional methods. Moreover, the catalyst can be recovered by simple filtration and reused several times without significant loss of activity.
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J.H. Clark, Green Chem. 1, 1–8 (1999)
C. Leonelli, T.J. Mason, Chem. Eng. Process. 49, 885–900 (2010)
K. Ramachandran, T. Suganya, N. Nagendra Gandhi, S. Renganathan, Renew. Sust. Energy Rev. 22, 410–418 (2013)
G. Cravotto, P. Cintas, Chem. Soc. Rev. 35, 180–196 (2006)
M.R. Nabid, S.J.T. Rezaei, R. Ghahremanzadeh, A. Bazgir, Ultrason. Sonochem. 17, 159–161 (2010)
S.J.T. Rezaei, Y. Bide, M.R. Nabid, Tetrahedron Lett. 53, 5123–5126 (2012)
S.J. Tabatabaei Rezaei, M.R. Nabid, A. Yari, S.W. Ng, Ultrason. Sonochem. 18, 49–53 (2011)
R. Breslow, Acc. Chem. Res. 24, 159–164 (1991)
S. Minakata, M. Komatsu, Chem. Rev. 109, 711–724 (2009)
M. Akizuki, T. Fujii, R. Hayashi, Y. Oshima, J. Biosci. Bioeng. 117, 10–18 (2014)
K. Saïd, Y. Moussaoui, M. Kammoun, R.B. Salem, Ultrason. Sonochem. 18, 23–27 (2011)
M. Bagherzadeh, M. Amini, P. Derakhshandeh, M. Haghdoost, J. Iran. Chem. Soc. 11, 441–446 (2014)
S. Bhattacharjee, W.-S. Ahn, J. Nanosci. Nanotechnol. 15, 6856–6859 (2015)
R.F. Heck, J.P. Nolley, J. Org. Chem. 37, 2320–2322 (1972)
Z. Zhang, Z. Zha, C. Gan, C. Pan, Y. Zhou, Z. Wang, M.-M. Zhou, J. Org. Chem. 71, 4339–4342 (2006)
C. Deraedt, D. Astruc, Acc. Chem. Res. 47, 494–503 (2014)
J.A. Przyojski, K.P. Veggeberg, H.D. Arman, Z.J. Tonzetich, ACS Catal. 5, 5938–5946 (2015)
Z. Donga, Z. Yea, Reusable Adv. Synth. Catal. 356, 3401–3414 (2014)
C.S. Yeung, V.M. Dong, Chem. Rev. 111, 1215–1292 (2011)
M.S. Cheung, F.K. Sheong, T.B. Marder, Z. Lin, Chem. Eur. J. 21, 7480–7488 (2015)
Y. Lee, M.C. Hong, H. Ahn, J. Yu, H. Rhee, J. Organomet. Chem. 769, 80–93 (2014)
N. Shang, S. Gao, X. Zhou, C. Feng, Z. Wang, C. Wang, RSC Adv. 4, 54487–54493 (2014)
P. Taladriz-Blanco, P. Hervés, J. Pérez-Juste, Top. Catal. 56, 1154–1170 (2013)
J. Lu, J.W. Elam, P.C. Stair, Acc. Chem. Res. 46, 1806–1815 (2013)
M.A. Betiha, H.M.A. Hassan, E.A. El-Sharkawy, A.M. Al-Sabagh, M.F. Menoufy, H.E.M. Abdelmoniem, Appl. Catal. B: Environ. 182, 15–25 (2016)
M. Hronec, K. Fulajtárová, I. Vávra, T. Soták, E. Dobročka, M. Mičušík, Appl. Catal. B: Environ. 181, 210–219 (2016)
F. Pinna, Catal. Tod. 41, 129–137 (1998)
C. Bara, E. Devers, M. Digne, A.F. Lamic-Humblot, G.D. Pirngruber, X. Carrier, ChemCatChem 7, 3422–3440 (2015)
P. Munnik, P.E. de Jongh, K.P. de Jong, Chem. Rev. 115, 6687–6718 (2015)
L. McMillan, L.F. Gilpin, J. Baker, C. Brennan, A. Hall, D.T. Lundie, D. Lennon, J. Mol. Catal. A: Chem. 411, 239–246 (2016)
S. Xue, H. Jiang, Z. Zhong, Z.X. Low, R. Chen, W. Xing, Micropor. Mesopor. Mater. 221, 220–227 (2016)
E. Taglauer, H. Knözinger, phys.Status.Solidi. b 192, 465-475 (1995)
L. Groenendaal, F. Jonas, D. Freitag, H. Pielartzik, J.R. Reynolds, Adv. Mater. 12, 481–494 (2000)
I.F. Perepichka, D.F. Perepichka, H. Meng, F. Wudl, Adv. Mater. 17, 2281–2305 (2005)
T.K. Das, S. Prusty, Polym.-Plast. Technol. Eng. 51, 1487–1500 (2012)
D. Astruc, F. Lu, J.R. Aranzaes, Angew. Chem. Int. Ed. 44, 7852 (2005)
S. Vinod Selvaganesh, J. Mathiyarasu, K.L.N. Phani, V. Yegnaraman, Nanoscale Res. Lett. 2, 546–549 (2007)
S. Harish, J. Mathiyarasu, K.L.N. Phani, V. Yegnaraman, Catal. Lett. 128, 197–202 (2009)
V.K. Veniamin, A.B. Tatyana, G.T. Elena, J. Solid State Electrochem. 17, 1621–1630 (2013)
M. Ilieva, V. Tsakova, W. Erfurth, Electrochim. Acta 52, 816–824 (2006)
D. Sthitaprajna, N. Munichandraiah, Electrochim. Acta 180, 339–352 (2015)
B.M. Choudary, M. Roy, S. Roy, M.L. Kantam, B. Sreedhar, K.V. Kumar, Adv. Synth. Catal. 348, 1734 (2006)
S.J.T. Rezaei, Y. Bide, M.R. Nabid, Synth. Metal. 161, 1414–1419 (2011)
M. Reza Nabid, S.J. Tabatabaei Rezaei, S. Zahra Hosseini, Mater. Lett. 84, 128–131 (2012)
J. Zhu, J. Zhou, T. Zhao, X. Zhou, D. Chen, W. Yuan, Appl. Catal. A: Gen. 352, 243–250 (2009)
L. Shao, Y. Ren, Z. Wang, C. Qi, Y. Lin, Polymer 75, 168–177 (2015)
J.G. Benjamin, W.K. Robert, B.K. Richard, L.D. Paula, Angew. Chem. Int. Ed. 46, 7251–7254 (2007)
M.R. Nabid, Y. Bide, S.J. Tabatabaei Rezaei, Appl. Catal. A: Gen. 406, 124–132 (2011)
H. Ahmar, A.R. Fakhari, M.R. Nabid, S.J.T. Rezaei, Y. Bide, Sens. Actuat. B: Chem. 171–172, 611–618 (2012)
H. Hosseini, S.J.T. Rezaei, P. Rahmani, R. Sharifi, M.R. Nabid, A. Bagheri, Sens. Actuat. B: Chem. 195, 85–91 (2014)
B.E. Warren, X-ray Diffraction (Dover Publications Inc, New York, 1969)
M. Nabid, Y. Bide, E. Aghaghafari, S. Rezaei, Catal. Lett. 144, 355–363 (2014)
G. Yang, Y. Zhou, H.-B. Pan, C. Zhu, S. Fu, C.M. Wai, D. Du, J.-J. Zhu, Y. Lin, Ultrason. Sonochem. 28, 192–198 (2016)
M. Ghotbinejad, A.R. Khosropour, I. Mohammadpoor-Baltork, M. Moghadam, S. Tangestaninejad, V. Mirkhani, RSC Adv. 4, 8590–8596 (2014)
R.R. Deshmukh, R. Rajagopal, K.V. Srinivasan, Chem. Commun. 17, 1544–1545 (2001). doi:10.1039/B104532F
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We are grateful to University of Zanjan Research Council for partial support of this work.
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Tabatabaei Rezaei, S. PEDOT nanofiber/Pd(0) composite-mediated aqueous Mizoroki–Heck reactions under ultrasonic irradiation: an efficient and green method for the C–C cross-coupling reactions. J IRAN CHEM SOC 14, 585–594 (2017). https://doi.org/10.1007/s13738-016-1007-7
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DOI: https://doi.org/10.1007/s13738-016-1007-7