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Letters in Organic Chemistry

Author(s): Khemais Said* and Ridha Ben Salem

DOI: 10.2174/1570178618666210521095042

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Ultrasonic Activation of N-arylation of Amines with Aryl Halides Catalysed by Iron (III)

Page: [627 - 635] Pages: 9

  • * (Excluding Mailing and Handling)

Abstract

A practical and promising protocol was developed for N-arylations of various aromatic amines. This protocol was carried out through the coupling reaction between various aryl halides and phenylboronic acid using iron (III). The processes are efficiently promoted by the catalyst system involving the environmentally benign iron (III) and the state PPh3. The advantages of this method are its versatility, convenient operation and low cost, along with the yields, which are remarkably improved under ultrasonic irradiation, and the high purity of the products obtained. The catalyst can be magnetic recycled via an external magnet and reused several times without considerable loss of its catalytic activity.

Keywords: Ultrasonic activation, N-Aryl amines, iron catalyst, sonicated, triphenylamine, Buchwald-Hartwig.

Graphical Abstract

[1]
Roberts, M.F.; Wink, M. Plenum Press: New York, NY, USA , 1998.
[2]
Buckingham, J.; Baggaley, K.H.; Roberts, A.D.; Szabó, L.F. C.R.C. press: Boca Raton, FL, USA , 2009.
[3]
Nakamura, E.; Hatakeyama, T.; Ito, S.; Ishizuka, K.; Ilies, L.; Nakamura, M. Org. React., 2014, 83, 1-210.
[4]
Legros, J.; Figadère, B. Nat. Prod. Rep., 2015, 32(11), 1541-1555.
[http://dx.doi.org/10.1039/C5NP00059A] [PMID: 26395292]
[5]
Piontek, A.; Bisz, E.; Szostak, M. Angew. Chem. Int. Ed., 2018, 57, 11116.
[http://dx.doi.org/10.1002/anie.201800364]
[6]
Correa, A.; Bolm, C. Angew. Chem. Int. Ed., 2007, 46, 8862-8865.
[http://dx.doi.org/10.1002/anie.200703299]
[7]
Chen, Y.J.; Chen, H.H. Org. Lett., 2006, 8(24), 5609-5612.
[http://dx.doi.org/10.1021/ol062339h] [PMID: 17107084]
[8]
Klapars, A.; Antilla, J.C.; Huang, X.; Buchwald, S.L.A. J. Am. Chem. Soc., 2001, 123(31), 7727-7729.
[http://dx.doi.org/10.1021/ja016226z] [PMID: 11481007]
[9]
(a) Jadhav, V.H.; Dumbre, D.K.; Phapale, V.B.; Borate, H.B.; Wakharkar, R.D. Catal. Commun., 2007, 8, 65.
[http://dx.doi.org/10.1016/j.catcom.2006.05.030]
(b) Huang, H.; Jiang, H.; Chen, K.; Liu, H. J. Org. Chem., 2008, 73(22), 9061-9064.
[http://dx.doi.org/10.1021/jo801942h] [PMID: 18937417]
(c) Wang, Z.; Fu, H.; Jiang, Y.; Zhao, Y. Synlett, 2008, 2540.
(d) Volla, C.M.R.; Vogel, P. Tetrahedron Lett., 2008, 49, 5961.
[http://dx.doi.org/10.1016/j.tetlet.2008.07.151]
(e) Mao, J.; Xie, G.; Wu, M.; Guo, J.; Ji, S. Adv. Synth. Catal., 2008, 350, 2477.
[http://dx.doi.org/10.1002/adsc.200800517]
(f) Ku, X.; Huang, H.; Jiang, H.; Liu, H. J. Comb. Chem., 2009, 11(3), 338-340.
[http://dx.doi.org/10.1021/cc800182q] [PMID: 19260652]
(g) Li, S.; Jia, W.; Jiao, N. Adv. Synth. Catal., 2009, 351, 569.
[http://dx.doi.org/10.1002/adsc.200800695]
[10]
(a) Carril, M.; SanMartin, R. Dom nguez. E. Chem. Soc. Rev., 2008, 37, 639-647.
[http://dx.doi.org/10.1039/b709565c]
(b) Hartwig, J.F. Acc. Chem. Res., 2008, 41(11), 1534-1544.
[http://dx.doi.org/10.1021/ar800098p] [PMID: 18681463]
(c) Surry, D.S.; Buchwald, S.L. Angew Chem. Int. Ed., 2008, 47, 6338-6361.
(d) Fischer, C.; Koenig, B. Beilstein J. Org. Chem., 2011, 7, 59-74.
[11]
Hartwig, J. Organotransition Metal Chemistry; University Science Books: Mill Valley, 2010.
[12]
Jiang, L.; Buchwald, S.L. Weinheim; Wiley-VCH, 2004, p. 699.
[13]
Surry, D.S.; Buchwald, S.L. Chem. Int. Ed., 2008, 47, 6338-6361.
[http://dx.doi.org/10.1002/anie.200800497]
[14]
Surry, D.S.; Buchwald, S.L. Chem. Sci. (Camb.), 2011, 2, 27.
[http://dx.doi.org/10.1039/C0SC00331J]
[15]
Buckingham, J.B. London; Volume: UK, 1994, p. 1.
[16]
Craig, P.N.; Drayton, C.J. Pergamon Ed, Press: New York, NY, USA. 1998, 8.
[17]
Negwer, M. Berlin, Germany , 1994.
[18]
Salvatore, R.N.; Yoon, C.H.; Jung, K.W. Tetrahedron, 2001, 57, 7785-7811.
[http://dx.doi.org/10.1016/S0040-4020(01)00722-0]
[19]
Phan, N.T.S.; Van Der Sluys, M.; Christopher, W. Adv. Synth. Catal., 2006, 348, 609-679.
[http://dx.doi.org/10.1002/adsc.200505473]
[20]
Yin, L. J. Chem. Rev., 2007, 107, 133-173.
[http://dx.doi.org/10.1021/cr0505674]
[21]
Guino, M. Hii. K.K.M. Chem. Soc. Rev., 2007, 36, 608-617.
[22]
Lamblin, M.; Nassar-Hardy, L.; Hierso, J-C.; Fouquet, E.; Felpin, F-X. Adv. Synth. Catal., 2010, 352, 33-79.
[http://dx.doi.org/10.1002/adsc.200900765]
[23]
Molnar, A. Chem. Rev., 2011, 111, 2251-2320.
[24]
Anderson, K.W. Tundel, R.E. Ikawa, T. Altman. R.A. Chem. Int. Ed., 2006, 45, 6523-6527.
[http://dx.doi.org/10.1002/anie.200601612]
[25]
Hartwig, J.F. Angew. Chem. Int. Ed., 1998, 37, 2046-2067.
[http://dx.doi.org/10.1002/(SICI)1521-3773(19980817)37:15<2046:AID-ANIE2046>3.0.CO;2-L]
[26]
Cahiez, G.; Avedissian, H. Synthesis, 1998, 1199.
[http://dx.doi.org/10.1055/s-1998-2135]
[27]
Saïd, K.; Moussaoui, Y.; Kammoun, M.; Ben Salem, R. Ultrason. Sonochem., 2011, 18(1), 23-27.
[http://dx.doi.org/10.1016/j.ultsonch.2010.04.007] [PMID: 20471902]
[28]
Mhamdi, L.; Said, K.; Rigane, G.; Ben Salem, R.; Moussaoui, Y.J. Tun. Chem. Soc., 2016, 18, 61-67.
[29]
Mhamdi, L.; Saïd, K.; Moussaoui, Y.; Ben Salem, R.J. Soc. Chim. Tun., 2013, 15, 149-162.
[30]
Said, K.; Ben Salem, R. Adv. Chem. Eng. Sci., 2016, 6, 111-123.
[http://dx.doi.org/10.4236/aces.2016.62013]
[31]
Mhamdi, L.; Said, K.; Atoui, D.; Moussaoui, Y.; Ben Salem, R. Chem. Africa, 2018.
[32]
Atoui, D.; Said, K.; Ben Salem, R. Turk. J. Chem., 2017, 41, 587-600.
[http://dx.doi.org/10.3906/kim-1701-31]
[33]
Yang, B.; Zhang, Z.; Yang, Z.; Ruan, J.; Luo, L.; Long, F.; Tang, D.; Ding, X.G. Front. Pharmacol., 2020, 11, 525.
[http://dx.doi.org/10.3389/fphar.2020.00525] [PMID: 32431607]
[34]
Yang, W.; Gao, Z.; Liu, X.; Li, X.; Ding, X.; Yan, W. Catal. Sci. Technol., 2018, 8, 4159-4168.
[http://dx.doi.org/10.1039/C8CY01225C]
[35]
Ghanbari, N.; Hoseini, S.J.; Bahrami, M. Ultrason. Sonochem., 2017, 39, 467-477.
[http://dx.doi.org/10.1016/j.ultsonch.2017.05.015] [PMID: 28732970]
[36]
(a) Chauvin, R.; Kagan, H.B. Chirality, 1991, 3, 242.
[http://dx.doi.org/10.1002/chir.530030406]
(b) Komatsuzaki, T.; Sakakibar, K.; Hirota, M. Tetrahedron Lett., 1989, 30, 3309.
[http://dx.doi.org/10.1016/S0040-4039(00)99229-3]
(c) Komatsuzaki, T.; Sakakibara, K.; Hirota, M. Chemistry Lett., 1990, 1913
(d) Hirota, M.; Sakakibara, K.; Komatsuzaki, T. Comput. Chem., 1991, 15, 241.
[http://dx.doi.org/10.1016/0097-8485(91)80012-B]
(e) Akai, I.; Sakakibara, K.; Hirota, M. Chem. Lett., 1992, 1317.
[http://dx.doi.org/10.1246/cl.1992.1317]
(f) Komatsuzaki, T.; Akai, I.; Sakakibara, K.; Hirota, M. Tetrahedron, 1992, 48, 1539.
[http://dx.doi.org/10.1016/S0040-4020(01)88712-3]
[37]
Tolman, C.A. Chem. Rev., 1977, 313-348.
[http://dx.doi.org/10.1021/cr60307a002]
[38]
Wu, W.Y.; Wang, J.C.; Tsai, F.Y.A. Green Chem., 2009, 11, 326-329.
[http://dx.doi.org/10.1039/b820790a]
[39]
Ling, X.; Xiong, Y.; Huang, R.; Zhang, X.; Zhang, S.; Chen, C. J. Org. Chem., 2013, 78(11), 5218-5226.
[http://dx.doi.org/10.1021/jo4002504] [PMID: 23675863]
[40]
Wolfe, J.P.; Buchwald, S.L. Angew. Chem. Int. Ed., 1999, 38, 2413-2416.
[http://dx.doi.org/10.1002/(SICI)1521-3773(19990816)38:16<2413:AID-ANIE2413>3.0.CO;2-H]
[41]
Hiraiz, Y.; Uozumi, Y. Chem. Commun. (Camb.), 2010, 46, 1103-1105.
[http://dx.doi.org/10.1039/B918424D] [PMID: 20126727]